1. safety

Italy is definitely a safe place to bring your family. The main thing to worry about here is petty theft, which can be avoided by staying vigilant and smart. Big cities and touristy areas are where you’ll hear of most pickpockets and bag snatching, but it’s important to exercise caution and beware of your surroundings in any new place. Traveling with kids can definitely make you vulnerable.. being a mom of two small kids I feel like I’m constantly digging through the diaper bag or rifling through a snack bag for something or other..it’s easy to get distracted when you have littles to constantly accommodate. I just try to be extra cautious about making sure all of our belongings are zipped up and tucked away. Throughout our entire month in Italy with the kids, I never felt unsafe or targeted though.

2. Italians love kids

I have never seen anything like it. Everything I read online before our trip said the same thing about how Italians love kids.. nothing prepares you for this actual reality though. The very first restaurant we dined out in, the server took Maggie (our 9 month old at the time) out of Ben’s arms and bounced her around while chatting. I remember being completely caught off guard and thinking something like, “..omg do not touch my kid.” It was hard to stay annoyed when he spent the entire duration of our meal doting on both kids and trying to make them laugh though. We realized very quickly that is what everyone meant by Italians love kids. It was constant throughout the entire trip too. Izzy would be given snacks while we waited for takeout, Maggie was given a free baby sized gelato, total strangers would come up at train stations to talk to the kids, and everyone was quick to help us. We do a lot of public transportation when we travel and Italians do not ask if you need help trying to lift your bags or stroller onto the train.. they just do it. Every city we were in someone would just casually grab the front of the stroller and help us off the train and then continue on their way. It was quite shocking initially, but by the end of our 4 weeks in Italy, we really appreciated how kind and helpful everyone was to us. Traveling with kids can certainly be tough, but everyone loving on our kids took an incredible amount of pressure off and was a huge reason why we loved our trip so much.

3. Italian food is super kid friendly

Pizza, pasta, focaccia, cheese, salami, GELATO.. not sure I need to say more. I know these aren’t the foods we want our kids eating everyday, but vacation isn’t everyday. To be completely honest, one of the main reasons we ended up in Italy for a month instead of anywhere else, was the food. We had initially thought we were going to Germany and then changed our minds maybe a month before leaving for Europe. Italian food was already something they were familiar with and loved.. taking them abroad for a month was already daunting, it was nice to not worry about a possible food struggle.

4. Great Climate

This was the other reason we changed destinations. Of course it depends on where in Italy you go and when, but for the most part, it’s going to be warmer than several other European countries. We were going for the month of May, so it was a pretty big swing from the beginning of the month to the end. But when comparing average temperatures, Central Italy was 5-10 degrees warmer than Germany that month. We aren’t generally a family that needs warm weather, but for our first international trip with the kids, we wanted to make sure we could spend a lot of our time outdoors comfortably. We rode bikes, explored new cities on foot, visited beaches, did scenic hikes.. anything to keep us outside.

5. Variety

Whatever kind of vacation you and your family enjoy, you can find it in Italy. You like skiing? Head north to the mountains and shell up at one of the numerous ski resorts. It’ll be incredibly cheaper than surrounding countries and Italy’s laid back ski resorts are known to be super family friendly. More of a beach person? You’ll find the most gorgeous and world renowned beaches throughout the south and up the coastline. Delicious food, wine, art, culture, history, the outdoors, the list goes on. Italy absolutely has it all.

6. Italian wine

Family vacations are not actually vacations for parents. They’re just parenting in different places. And in a lot of ways, they’re even more labor intensive with busy itineraries, long travel days, an upside down routine, and if you normally have help at home in the form of daycare or grandparents, on vacation you’re at it alone. Totally worth it, but it’s still a lot. Wine definitely helps, lol.

7. Public Transportation

You can totally pull off an entire Italy vacation without spending time in a car. Not saying you want to, but it is possible. The train and bus system covers a lot of ground and it’s nice to know you can rely on it for most destinations. They’re also very easy to navigate and kids under 4 travel free on Trenitalia. It doesn’t guarantee your toddler his/her own seat, but the trains don’t usually book up. We only had our toddler on our lap maybe once and had loads of travel days. Most trains do offer a child rate from ages 4-11 as well. One thing to note: if you’re mostly thinking about small, Tuscan villages, they most likely won’t have train stations or bus routes. You can do organized tours or hire a driver if need be. Check with their policy about car seats beforehand.

8. walkable

Italians walk everywhere and Italian cities are absolutely set up for the pedestrian. A lot of small villages in Italy don’t even accept cars into their Old Towns. It’s pretty great if you plan on doing most of your exploring on foot. You don’t realize the luxury of not worrying about cars until you have a very active toddler on your hands. If you’re planning on using a stroller most days, keep in mind that a lot of the roads are old cobblestone, which can pose a challenge depending on your stroller. We brought a single jogger for both our kids and couldn’t be happier with the decision. You can read a post here detailing how and why it worked for us.

9. Old Cities feel like Giant Playgrounds

Small kids might not care about history, but they do care about castles, piazzas, fountains and fairy tales. Our toddler loved exploring “hidden” alleyways and stairwells throughout villages and running after pigeons in the open piazzas. I’d be lying if I said my husband and I didn’t enjoy it just as much though. It was so much fun wandering through medieval roads and feeling like we stepped back in time. We definitely appreciated experiencing a piece of history while Izzy enjoyed how many Elsa castles there were.

10. Museums

Museums are everywhere in Italy and loaded with the most fascinating things. Since we were traveling with small kids, we were hesitant to visit them though. Expensive entrance fees and bored/cranky little ones make for a giant waste of time and money. However, the cool thing about Italian state museums is that kids under 18 are free. You still have to obviously pay for your own entrance, but it makes museum visits more affordable and less of a bummer if you need to end your tour short. Keep in mind this is only for State Museums.. “Museo” and sometimes city owned museums.. “civic” or “municipal”. Privately owned museums most likely will not offer a discount.

jogger/carrier

Instead of bringing a double stroller, we chose to bring a single jogger stroller and our Bjorn baby carrier. The decision to do this really couldn’t have been any better for us. The jogger was mostly used for our toddler, while the 9 month old usually sat in the carrier. However, we planned on using the stroller for whoever needed it at the time. For instance, if our baby was due to nap or getting fussy in the carrier, we would shift her into the stroller and have our toddler either walk with us or carry her on our backs. Having the jogger with us instead of our other strollers was especially nice too. I loved having it because it wasn’t too big like our tandem would have been, but it was also big enough to take on cobblestone and uneven terrain. The bottom basket was super convenient to have as well (think grocery shopping and carrying things back) and the sturdiness of the stroller in general was a life saver during travel days. It allowed us to attach our diaper bag to it or even pile up our backpacks when the kids weren’t in it. I considered buying a travel stroller for awhile, but after bringing our jogger and having such success, I don’t think we will. To read more about why we chose to bring our jogger and how it worked for us, you can read my blog post here.

Clip on highchair

This is definitely not for everyone, but it certainly was a game changer for us and one of the best things we brought. Maggie turned 9 months a few days into arriving in Italy. She was at a point where experimenting with food was important, so I wanted to make sure she could easily feed herself and reach food on the table. A clip on highchair was the answer for us. I was initially hesitant because it seemed bulky and extra, but it was actually super easy to pack and didn’t take up much room. It breaks down into pieces and depending on which one you buy, you may even have one that’s entirely collapsible. and lies flat. Ours had a metal bar that fit snug in between clothes in a suitcase, and two push up locks. It ended up being quite compact. We brought this specifically for our airbnbs. Once we checked in, we would set it up and keep it in place until we checked out. It was the perfect set up for us. You can always request highchairs through airbnbs and a lot of times, if they offer cribs, they also have access to highchairs. But in my experience, requesting a highchair will always narrow down the search results that much more. So I prefer to bring our own and maybe have a better accommodation.

bed bumpers

We transitioned Izzy to a big girl bed before our trip abroad on purpose. We were planning on staying in airbnbs and not traveling with our own travel crib. So this meant narrowing our search down to listings that had cribs/travel cribs available. If we had to find two cribs, we probably wouldn’t have had much luck. So about a month before our trip, we moved Izzy to a twin bed to get her ready for 5 weeks away sleeping in big girl beds throughout Italy. I specifically ordered inflatable bed bumpers so we could deflate them and take them with us as well. This is something I am so glad we did. She obviously needed bumpers in her bed at home, and these killed two birds with one stone. They were so easy to travel with and blowing up took less than a minute. We actually got away with only taking one as well. Most the beds in our airbnbs were up against walls so we opted for one and saved room in our bag.

wash cloths

Sounds ridiculous, but with kids you will always need something to wipe them up. With traveling in Italy especially, we were eating plenty of red sauce and I wasn’t about to stain someone else’s towels or wash cloths while cleaning up my kids. I’m partly considerate, but also, people will charge you for messing up their linens, lol. This is even true in some hotels if you remove your makeup and ruin their towels. Just not worth it in my opinion. We brought maybe 3 wash cloths and will definitely be bringing them again on our next trip.

familiar snacks for first week

You can obviously load up on snacks once you get to your destination, but familiar snacks from home are key. Both our girls ate pretty well in Italy, but the first week was trial and error. We were so lucky we brought plenty of pouches and baby snacks with us. The first couple of days were quite the adjustment and our kids clung to anything familiar. At one point, Izzy was even refusing to eat pizza, which was so unlike her. It took Ben figuring out that she wanted the pizza slice she could “fold in half like at home” and he went half way across town to get her a different pizza that she devoured. Having something that feels/tastes like home helps ease into being away. Side note- you can bring liquids through security for your small kids. I even had a few juice boxes in our bag.

Thermometer / Tylenol

If you’re traveling far with a baby and/or toddler, chances are a thermometer and Tylenol are already on your packing list. And if not, add them. They’re those items you bring and hope not to use. We used both the very first day we arrived in Italy. We don’t use Tylenol often, in fact, we’ve only really given it to the kids when they have had fevers. Sure enough, as soon as we got to our airbnb in Rome, we took Maggie’s temperature, she had a fever, and we gave her the Tylenol. We used it that one time and didn’t have to use it for the rest of the trip. Soo glad we had it when we needed it though.

What We Didn’t Love

Cloth highchair

We brought two highchairs to Italy. The clip on one I mentioned above, and a cloth one that straps to chairs and is super portable. The intention with the cloth one was to keep it in the diaper bag for restaurants and on the go. We had read that most Italian restaurants don’t have highchairs and we didn’t want to risk limiting her to our laps. If we were going for a week we would have taken our chance and fed her on our laps or in the stroller.. but a month was too long to have her potentially too distracted and not able to feed herself. Plus, if you read my post, Why We Didn’t Dine Out in Italy, you know absolute chaos would have ensued with her on my lap. But anyway, don’t take a cloth highchair. The only time we used it was at our one airbnb when the table couldn’t accommodate the clip on.. In the end, we made it work on a different table anyway. The cloth highchair was useful for the day or two in between, but that was honestly it. The idea behind it is great, but it just fell short for us. Since it straps to a regular chair and she sits on the seat, she isn’t able to feed herself because she’s sitting so low. Also, the few restaurants we dined out at did in fact have highchairs. So we didn’t need it anyway. Luckily it doesn’t take up much space in your bag since it rolls up.. but even so, I won’t be taking it on any future travels.

formula

If your baby is flexible with formula and you’re spending significant time away, you can buy formula in Europe. You won’t find it at the grocery store, but rather the local pharmacies. I wouldn’t recommend this though if you’re staying off the beaten path in smaller towns. I’m sure they would have something, but the risk is much too great in my opinion. Maggie transitioned to strictly formula not long before our trip. Of course, this coincided with starting to eat more solids. We transitioned her to a hypoallergenic formula since she was having some issues with eczema and we were starting to suspect possible food allergies. Because of this, we wanted to make sure she had everything she needed, and packed enough bags for the entire month away. As the end of our trip was approaching though, we decided to extend an extra few days, making the entire trip 5 weeks. We were short on formula by only a day and a half maybe, but we were also ending our trip in a bigger city and knew we could find everything we needed. We even surprisingly found a much greater variety than we expected. If I had known that I could very easily find such a variety of formula ranging from organic, hypoallergenic, dairy replacements, and so on, I probably would have only brought enough formula for half the month and picked up what we needed when we arrived in Rome. Side note- the European brands Holle and Hipp that a lot of American families are familiar with were not at the pharmacies we visited. This is not to suggest you wouldn’t be able to find it, but just an observation.

carrier for toddler

This was just dumb. The thought behind this was that we were bringing a single stroller for two kids to take turns in and having a carrier for those extra tiring days would be helpful. Plus, we had one destination that was going to be a lot of stairs, both getting to and from the airbnb, but also all around the town. We were staying there for 6 days and planned to mostly leave our stroller at the house during the day. So we thought both carriers would come in handy. Turns out, we used the carrier for our toddler only once and that was in an entirely different town. It also lasted only 10 minutes before our toddler wanted to get out and walk.. so we were stuck wearing it even though we weren’t using it. In the end, it’s just way easier to pick them up and hold them when they need to be held. It would have been better to bring a carrier that worked for both of them, but sadly, our little one doesn’t do as well in the carrier that can accommodate her older sister. And since we knew we would mostly be carrying Maggie, we had to bring the carrier best suited for her. It’s not a terrible thing to have certain items for ‘just in case’ moments, but considering the space it took up in our bag, it was not worth it.

Too Much Clothing

I never used to overpack when I was a flight attendant or backpacking solo.. but every time I go somewhere now I seem to bring a couple things I don’t need or never wear. Maybe it’s age or becoming a mom, but I always have “just in case” items now. We left for Italy early May and came back mid June, which meant we were arriving in 60 degree weather and leaving in closer to 80 degree weather. I mostly focused on layering for this reason, but I was still worried the kids wouldn’t be warm enough initially. Rain was expected the entire first week as well, which had me remembering the constant chill we’ve experienced in some European airbnbs. That all being said, I brought lots of options. It wasn’t crazy, but I still wish I left a few things at home. If you’re going somewhere with a washing machine or do hand washing while traveling, you really don’t need all the extras. I am happy we brought our toddler’s rainboots and raincoat, but extra sweatshirts, onesies, and bibs were unnecessary. If your kids are messy like mine, chances are you’ll be constantly washing things anyway.

Which stroller we were bringing to Italy was probably the hardest decision we made for the entire trip. Not destinations, or what accommodation to book, but strollers. We currently own two strollers- the Baby Jogger City Mini GT, which is a single jogger, and the Mockingbird double stroller, which is a tandem. I had thought about purchasing a travel stroller for our trip, but I was reluctant to buy something without having enough time to use it beforehand. Sounds funny, but you don’t realize how obnoxious a stroller can be until you’re pushing one with a crying baby, the wheels are getting caught, the ride is bumpy, and the seat doesn’t recline enough. Plus, we were going for a month. So whatever we were bringing, we were stuck with for awhile.

In addition to our two strollers, our friend also offered up her Evenflo tandem double with carseat. This was tempting since it would open up some options for us. We hadn’t considered taking a carseat.. Maggie would be listed as a lap child on the flight, and we planned on taking public transit while traveling. But with a carseat/stroller combo, we could potentially take a Flixbus, which requires a carseat (flixbus is essentially like a greyhound bus in the US.. larger charter buses for longer trips), we could pop it in and out of cabs, and also already have our own for a possible rental car while in Tuscany. So it was intriguing. In the end though, we decided against it. It was just too much to take and we were trying to simplify.

Our decision to take our single jogger basically came down to sturdiness. Both strollers had great wheels for cobblestone and uneven ground, but the tandem aspect of our double had me doubting it’s durability. It’s a solid stroller for sure, but seats that clip into attachments worry me with the flight. Something could just easily snap if mishandled. And then we’d be stuck with a broken stroller or a seat that doesn’t clip in securely. The single jogger was way smaller than the double as well.. still big for European standards, but loads smaller than the tandem double. Which looking back is hysterical that we even considered taking the tandem double.. it would've felt like maneuvering a cruise ship there. But anyway, the jogger worked beautifully for us and we plan to take it again on our next trip abroad in September.

This is also not by any means a post to deter you from purchasing or using a travel stroller. People love them.. they were honestly everywhere in Italy, and there’s a reason they’re called travel strollers. I’m only sharing our thoughts and experience because I don’t want you to feel obligated to buy a travel stroller if you already have something that can easily work for you. I included below the four big reasons why and how the single City Mini GT worked for us as a family of four going to Europe for 5 weeks.

The Flight Over

One of the big sells of a travel stroller is that it’s lightweight and collapses small enough to fit in the overhead bin of an airplane. People love this. I’m actually not into though. Traveling with children means we’re already traveling with more bags, which means we need more overhead bin space already. Securing that extra space means getting down to the plane in the earlier stages of boarding. This is typically easy to do when you have small kids in tow by the way.. gate agents are usually pretty accommodating when they see you have littles. If you aren’t able to get down though, you risk losing out on those overhead bins near your seat. Not a huge deal, but something to consider. I very much dislike finding and making room in overhead bins so adding a travel stroller sounds miserable to me. Instead, I like to use our stroller through the airport and then gate check it at the plane. You literally drop it right outside the boarding door and once you land they unload it for you and hand it back as you’re deplaning. You don’t have to check it at the check in counter outside security or get it at baggage claim. Of course, this is an option, but I prefer to keep it and do plane side checked.

The WHEELS

Jogger stroller wheels are king in my opinion. They’re always bigger, the ride is smoother, and I never have to worry about any kind of terrain. It’s a win win for parents and baby. Yes, I know we’re talking about strollers and not cars, but keeping a baby happy and sleeping while on the go is such a beautiful thing. We even took the stroller on trails outside San Gimignano and it was a huge success. At one point, Benjamin was pushing the stroller up a rocky, dirt trail. I highly doubt anyone else has taken a stroller up this stretch, but it worked for us!

Storage

The basket underneath the stroller was so helpful! To be honest, our double stroller’s underneath basket is even bigger and it was one of the few reasons we were considering taking it. But our single held for for sure! Traveling for such a long amount of time means we are going to grocery stores often. And in addition to groceries, we’re grabbing diapers, giant water bottles, and wine (lol). Having a decent sized basket to stow the bigger and heavier items was a total game changer.

Additionally, since the jogger is bigger than a travel stroller, it holds more in general. You don’t realize clipping a diaper bag to a stroller is luxury until you are lugging extra weight around with you at all times. On travel days, we moved through towns and on/off public transportation with two large backpacking backpacks, a diaper bag backpack, a jansport backpack, a roll abroad suitcase, the stroller, and two kids. While on trains, and sitting in train stations, we had Maggie in the baby carrier, Izzy hanging out in a regular seat or bench and we were able to stack a few bags in the stroller. This was so helpful just to keep better track of everything. Touristy areas in Italy are known for pickpockets so consolidating our things was a bit relieving.

One Stroller Two Kids

Having one stroller for two kids was the main thing we were worried about and it didn’t even come close to being an issue for us. Obviously all kids are different so I can’t say you’ll have the same experience.. but hopefully you do. Our toddler was mostly in the stroller and our 9 month old was mostly in a carrier. When our toddler insisted on walking or exploring, we would move our baby into the stroller for a change of scenery. If we were out and nap time hit for the little one, she would take the stroller and Izzy would either walk, or one of us would carry her. Basically, whoever needed the stroller, got the stroller and there seemed to be some weird understanding about it.

When most people think of Italy they immediately think of the food. Sitting out with an aperol spritz and a bruschetta board or twirling pasta with a glass of chianti. I’d be lying if I didn’t think of that too. In fact, when I first started planning our month in Italy, I envisioned doing mostly that. So it’s still funny to me that it was not our reality. In an entire month away in Italy, we counted 8 times that we attempted a dine in situation. That includes simply sitting out in a piazza with a drink and appetizer too. If we sat somewhere and relied on table service, it counted. And honestly, out of all 8, only 3 were very.. not good, lol. But even “only 3” can have a lasting effect on your anxiety and have you rethinking your next meal out. Don’t worry.. I’m going to share those three experiences throughout this post.. and hopefully not deter you from taking your small children anywhere ever again. You may be shaking your head thinking that sounds absolutely insane. Insane to only dine out 8 times in Italy, and insane to let 3 not great experiences impact the rest of our trip. Yeah, me too. But when you have a 9 month old and a 2.5 year old, things get tricky. Sure you can do it, but it’s not fun. And vacation is supposed to be (sorta) fun. So we tried our best to accommodate all of our needs and once we shifted our expectations, we were all a lot happier.

One of the reasons we chose to do our vacation in Italy was the food. You can read more on why we chose Italy and how we decided on our destinations here. Of course there were other factors, but it mostly came down to the food. With a baby and a toddler, Italian food is king. A week before we left on our trip, our toddler was telling everyone that we were going on vacation to eat pizza. She wasn’t wrong. And she was quite pleased as she shared the news. Of course she didn’t include where we were going, and we didn’t bother to add it in either.. so I’m still wondering what people must’ve thought. But oh well, who cares. We went on vacation and did eat an incredible amount of pizza. So there’s that. Pasta made up the other half of our diet, lol. Izzy fell in love with gnocchi and both the kids now love pesto. We stayed in the pesto region for awhile so it quickly became a staple. Maggie was obsessed with focaccia and I swear that baby ate more than we did every morning. It was so nice to be in a new country for the first time with the kids and not have to worry about food. If you have small kids, you know what I mean. New food can be tough.

Our Children

All that being said, eating out in restaurants was not our favorite. Small kids get bored, they choose to be picky right when you think you’ve nailed down their favorite foods, they get distracted, and it can just be chaotic. The very first meal out we did was in Siena. It was the most typical Italy restaurant experience you could imagine. In a good way, of course! The server was all about the kids, checking in on them and making them laugh, we ordered more food than we needed just to try all the things, everyone was in a good mood, and we also somehow didn’t get caught in the endless rain that day. It was as if the sun came out for just the amount of time we needed to get to and from the restaurant, creating this beautiful illusion that we were meant to be a family who dines out. We were elated. And then we went out a second time. We sat outside at a cafe for lunch, which turned out to be super distracting for a toddler. Instead of eating, Izzy kept hopping out of her chair and wanting to explore and stare down any passerby. That would have been totally fine had we been in a somewhat confined patio space or something. But instead, the cafe’s few tables sat along the main walking street. Lesson learned. Trying to keep an eye on Izzy and keep her nearby meant I was distracted myself.. and like a bandit, Maggie swiped my cappuccino off the table not 5 seconds after the server placed it down. Unlike our first server, this one did not like our children. Or us. And this sad wasted cappuccino marks the start of a trend that lasted the entire 5 weeks of our trip. I swear her wingspan grew an additional foot whenever I had any sort of beverage in my hand, on a table, or really anywhere for that matter. She whacked countless drinks out of my hand while in the carrier.. including a giant 6 Euro cappuccino that I hadn’t even taken a sip from yet. WHACK. All over the floor at the Monaco train station, which was maybe the most pristine, quiet, and least crowded train station I have ever experienced. And did I mention it was huge? Like, American size. The biggest caffeinated beverage we found during our whole trip.. all over the floor. So that happened. But back to the cafe.. this really doesn’t sound overly dramatic, I know. But picture this: Service is taking forever, Isabelle is losing interest and starting to slink out of her chair, Maggie is starting to fuss, server drops beverages, said beverage is swatted all over the table and my lap, server is pissed, Ben is trying to clean up, I’m trying to make sure coffee won’t stain the only jeans I brought, IZZY COME BACK OVER HERE, Maggie starts screaming, Izzy won’t listen, sandwiches are placed down, Izzy isn’t hungry anymore, I get up to pace with Maggie, Ben is shoveling sandwich in his mouth as fast as possible, a car turns down the one way, tiny, mostly pedestrian street our table is on and comes head on with another car, they’re yelling in Italian at each other, the one driver tries to inch over and starts driving over the potted plant next to our table, IZZY SIT DOWN, I have Maggie in the carrier trying to move the plant, more yelling in Italian, Maggie crying, Izzy.. where is Izzy? Izzy has to go pee pee, Ben takes Izzy inside, I’m pacing with Maggie, hopefully no one steals the stroller, my pants are still wet and brown, why the ef did we do this? That mostly sums it up.. I hope you read it in your head very quickly like the giant run on sentence it is.. because that’s how it felt. That was the first not fun experience.

Nap Time + Wake Windows

I read something the other day about considerations when traveling with small kids. It basically talked about if your child has a strict nap schedule or cant’t sleep in a stroller they would recommend not taking said child to Italy. Well that’s rather harsh, but I do understand the hesitation. Although we struggled with Maggie’s sleep schedule and refusal to sleep on the go, we wouldn’t have chose to skip our trip. It did make things more challenging though. At 5 months old, we did sleep training with Maggie and it’s been the biggest blessing and biggest curse. The girl loves her sleep more than anything and her naps are like clockwork. Up two hours, down two hours. If she doesn’t get her quiet, dark room for her nap though, she refuses altogether and will make a point to let you know she’s not happy about it. She’s okay if she’s moving in the stroller or carrier, but if we’re sitting somewhere it’s game over. It took some time to figure out a routine that worked for us. Trying to squeeze getting out of the house, getting to a restaurant, eating, and wrapping it all up into a 2 hour window is not the easiest. We tried our best to be ready to leave as soon as she would wake up, but with a 2.5 year old sometimes it just didn’t happen. Our second failed lunch out happened in San Gimignano. Again, we sat outside. This is usually the safe option for us. If we need to walk away with one of the kids, outside is always easier than being stuck inside. Our lunch here was similar to our lunch in Siena in that the chaos of many moving parts and trying to move things out of Maggie’s reach is pretty much the base line of every meal out. But instead of a spilled cappuccino, angry server, and drama with drivers, we had smashed plates, Izzy insisting on eating pizza off the ground, and a very crowded seating area with judgey customers. To top it off it was raining and although there was a giant awning, we didn’t realize we placed the stroller under a hole in the awning and by the end of our meal the entire stroller was soaked. We were definitely jiving the first half of the meal.. we even got to the actual eating part before it took a quick turn. Maggie started to get tired and frustrated and again, somehow ninja’d us. We specifically made sure she couldn’t reach Izzy’s plate, but did not consider the placemat. Like a magician pulling the tablecloth out from under a set table, Maggie ripped the placemat out from under Izzy’s plate and water glass. Except it wasn’t a skillful execution. Everything smashed onto the ground and we were immediately those people making a mess and causing a scene. Luckily the server was so sweet, but Izzy was devastated because the only piece of pizza she was interested in was now on the ground. I had to take Maggie for a walk and I’d be lying if I said I wasn’t on the verge of tears.

Italians Eat Late

Before we set off on our trip we already knew dinners out wouldn’t be happening and we planned on either doing carry out back to the house or cooking. Italians eat later dinners and most restaurants close after lunch until about 6-7 PM. Considering Maggie goes to bed at 7 and Izzy between 730-8, this would not be an enjoyable or realistic option. However, our Airbnb in San Gimignano happened to be located right next to a restaurant with the most incredible views of the Tuscan hills. And as it would turn out, our Airbnb host’s family ran it. He offered to make us a reservation and since we were staying literally right next door, we figured we would give it a shot. Our reservation was set at 6, right when they opened. We were a bit anxious about how things would go down, so we tried to line up Mag’s naps as much as we could to get her waking up right at our reservation time. We even went as far as Ben and Izzy going down to get situated at the table and letting Maggie sleep a few extra minutes. We had already decided on our meal and were going all out with first course pasta dishes, followed by mains. SO MUCH FOOD. I woke Maggie up, got her ready, and we set out to join Ben and Iz. Our host made sure we were totally set up with one of the best tables on the outdoor patio. The view was absolutely gorgeous and the patio was packed by the time Maggie and I got there..which was only a few minutes after they opened. We order some wine, put in our food order, Maggie’s just chilling in the stroller with some toys, and Izzy is snacking on French fries while we wait for our first course. It honestly felt magical. I mean, panoramic views of the tuscan hills with a glass of chianti, content children, and Ben and I just sitting there taking it all in and feeling so grateful. It was perfect. Pastas were brought to the table and we all dug in. We were all in absolute heaven. Everything was so delicious and Maggie was still just hanging out, totally content. Mains were brought and right as we were about to try them, Isabelle vomited all over the table. Over and over and over. At one point Ben had his hands cupped in front of her mouth and vomit was piling up so high it was spilling out of his hands. I was scooping vomit into cloth napkins and hiding them in the under basket of our stroller. I tried my best to clean up what I could while trying my hardest to be super discreet. Eventually I just grabbed Izzy and ran back to the Airbnb leaving Ben and Maggie behind. Ben paid the bill and 120 Euro later we were emotionally destroyed and still hungry. The entire time we were on edge about Mags and didn’t even see this coming.. I still wonder how many people saw and were absolutely horrified.

What we did instead

Counter service, picnics, carry out, and cooking back at the airbnb! There were actually quite a few options and we didn’t feel we missed out on much. We ate in parks, on beaches, at playgrounds, on the go, back at the airbnb, and so on. A lot of places we went had counter service and tables though. So it felt like we were dining out, but we were paid up and could leave if we needed to. It was a win win. A typical day depended on what town we were staying in at the time and what the plan was for that particular day. We usually did breakfasts at the airbnb.. it was faster than going anywhere with the kids and it’s also a great way to save money. Such an easy and inexpensive meal to accommodate with items from the grocery store. However, one of our airbnbs during our trip was three doors down from a bakery. So for instance, that stay we did breakfasts out. We literally woke up, dressed, and immediately headed to the bakery. We took breakfast to go and would immediately start our day. That stretch of the trip was obviously earlier starts, which was nice too. Lunch was almost always out. We would grab something and have some sort of picnic, or score a table outside where we picked up lunch. My favorite was bringing food to the playground. Eating delicious food and watching your happy kid run around a playground pairs nicely as it turns out. Dinner was a mixture of carry out and cooking back at the airbnb. Like mentioned earlier, our kids are in bed between 7-8, which is when a lot of Italian restaurants are opening for dinner service. We typically would cook something up for the kids and then some evenings, Ben would run out for carry out for us while I did bedtime. This is how we were able to still explore the cuisine, check off some of the restaurants we thought we wouldn’t be able to experience, anddd get some date night energy into our family trip. Note that not all restaurants in Italy will accommodate carry out though.. we struggled a bit in San Gimignano and were screwed 2 different nights without dinner because we hadn’t planned ahead. So just keep that in mind.

Had I known we would’ve only dined out 8 times in 5 weeks I probably would’ve thought the quality of our trip would have greatly suffered. We love eating and that’s mostly what we do when we travel. Truth be told, it really didn’t impact our trip much at all. Sure, it would’ve been nice to go out more here and there, but it’s not really something I’m still thinking about or wishing we could’ve changed. We did what was best for our family and it worked. Lowering expectations with two small kids was probably the key.

The Leaning Tower of Pisa receives over 5 million visitors every year from all over the world. Although there’s more to see in the Piazza del Miracoli, it’s the tower that everyone knows and thinks of when they hear “Pisa”. The tower was completed in 1399 and started leaning way before it was even finished. Architects noticed the slant in 1173 after only 3 of the 8 stories were completed. Soft soil and a shallow foundation were the culprits. However, after the tower settled for some time, the project was continued and the slant was compensated with shorter upper floors. This created a curve as well as the infamous lean we all love. Architecturally, the tower is a bit of a disaster, but that’s what makes it so unique, interesting to see, and globally recognized. Even my toddler knew about the Tower of Pisa from Little Einsteins.

So chances are, Pisa may already be on your bucket list. The best way to do Pisa, in my opinion, is as a day trip. If you happen to have extensive time, go ahead and make a night of being in a new city. But honestly, I did not fall in love and wish we had stayed to explore more. So that tells me a day trip was perfect for us. We did the Square of Miracles, meandered down side streets, crossed the river, had lunch, found a carousel for our toddler, and jumped back on the train. It was a short and sweet day and I would probably do it again as a day trip rather than an overnight.

Pisa is near the west coast in Tuscany and super easy to add into any Tuscan itinerary. We stayed in Lucca and it really couldn’t have been any easier. I like to use the trainline app for all my tickets and definitely recommend it. We usually rely strictly on wifi while traveling, so I’ll buy tickets on my phone before leaving the airbnb or wherever we may be before heading out. It’s so nice strolling into the train station and not worrying about tracking down a ticket machine, hoping it’ll take your credit card, and anxiously doing it all before the train gets there.. especially when you have kids with you.

Opening Hours

The tower is open everyday from 9am - 8pm.

Summer hours are 830am - 10pm June17th - August 31st.

June 16th closes early 830am - 530pm.

Getting to Pisa From Lucca

If you’re staying in Lucca, Pisa is an absolute must. Whether it’s for a couple hours or a full day, it’s definitely something you should squeeze in and see. It’s only 30 minutes on the train and the train runs for the most part every 30 minutes or so, with an exception for a two hour lull between 10am-12pm. The train will run you $4.26 per person with children under 4 riding free. Most directions have you going all the way to Pisa Centrale, but we actually got off at Pisa San Rossore and much preferred it. It’s only an 18 minute walk to the tower and it’s much quieter and easier to maneuver and navigate. If you have a stroller you’ll appreciate this. If you continue onto the Pisa Centrale stop, it’s only a few minutes more of a walk, but it definitely felt longer to us. Instead of walking down the wide sidewalk, making a right turn and seeing the tower in the not so far distance, you’ll have to walk through the busier town, cross more streets, go over the river, and then continue on more narrow sidewalks. Of course, if you plan to get a meal or coffee beforehand, Pisa Centrale is your best bet.. much more going on.

Getting to Pisa From Florence

From Florence, the train takes about 50-60 minutes depending on the train and it runs on average, about every 20-30 minutes. One ticket will cost you $10.25 and again, kids ride free in Italy until the age of 4. From 4-11, tickets may be discounted though. If you decide to get off at the Pisa San Rossore stop, it’s the next stop after Pisa Centrale. The train ticket costs the same regardless what stop you get off at though.

Tickets

Tickets to the tower are done by reserving a specific time slot. You can do this at the ticket office in Pisa, but I recommend purchasing tickets online before you go. There’s nothing worse than arriving at your destination and realizing you have to wait around longer than you had hoped.. or worse, completely missed your opportunity. You can reserve tickets online up to 20 days ahead of time. If you decide to buy tickets in person, you can find one ticket office in the Sinopie Museum, and the other at the Palazzo dell’Opera del Duomo. A ticket solely to the tower will cost you 18 Euro, whereas a complete visit to the tower, Cathedral, Baptistry, Camposanto, Opera del Duomo Museum, and Sinopie Museum costs 27 Euro. This can be broken up and you can pick and choose what you would like to see though. Whether you’re purchasing tickets strictly for the tower, or adding the Baptistery or Camposanto, tickets to any of these will automatically get you into the Cathedral. AS LONG AS YOU HAVE A TICKET TO ANYWHERE, YOU CAN VISIT THE CATHEDRAL FOR FREE. A break down of all the prices can be seen here. I’ve read that the official website can be a bit wonky and people have had trouble with payments and confirmations. For this reason, I would recommend booking through a third party site such as Viator to avoid any potential issues. Their prices are never outrageous and there are always different options.

Things to Note

• Children under the age of 8 are not permitted to climb the tower.

• It’s a total of 294 steps. They are slanted and can be slippery.

• Arriving 20 minutes before your scheduled time slot is recommended.

• Bags/belongings are not permitted up the tower. There is a free bag drop though.

Most write ups on visiting the tower suggest getting there right as it opens to beat the crowds that show up closer to 10am. However, we arrived at 9:20 and the entire piazza was already filled with people. Obviously it all depends on the day, but that was a Thursday morning in late May. Additionally, at that hour (and time of year), the sun is sitting riiiight behind the tower, which made not only photos difficult, but admiring the tower wasn’t so easy either. I kept thinking I was going to go blind, lol. Our two year old mostly hid in her stroller with her sun shade all the way down while I tried to wear her sunglasses and sunhat. Ben had mentioned that if we did it again, he would have us enjoy our day in Lucca and then head to Pisa in early evening. The sun wouldn’t be so harsh on our eyes, our kids wouldn’t be melting, we could get beautiful pictures in much better light, and then finish off our visit with dinner in Pisa. This is honestly a plan that excites me and I think we will try it out next time we’re in Tuscany. One thing to keep in mind with day trip destinations is that day trippers typically leave in the afternoon. So this plan would shave off plenty of tourists and slim down the crowds quite a bit too. Otherwise, if that’s too late for you, I would recommend getting to the tower much earlier than the 9am opening time to beat the crowds. You won’t be able to climb the tower yet, but you can wander the Piazza and snap photos before everyone floods in. Then just grab breakfast and head back for your scheduled time slot.

Traveling with little ones is tough. It doesn’t matter how prepared you are, literally or mentally, a toddler or baby will always bring the element of unpredictability. We’re currently just shy of three weeks into our 4 week vacation, and although everything is going relatively smoothly, every time I seem to let my guard down, chaos ensues. Isabelle seems to have an accurate radar for when I’m starting to feel comfortable and confident.. and every time, she has a meltdown to even me out and keep me on my toes. It’s absolutely infuriating. We knew this “vacation” would not be a leisurely one, or relaxing in the slightest.. but I didn’t think my anxiety would be this revved up. Don’t get me wrong, the good has outweighed the not so good, and I would and will (possibly regretfully) do this again, but the tension I feel some days waiting for the shoe to drop is definitely present. We traveled from San Gimignano, Italy to Lucca yesterday with a bus ride, two train rides, and a 40 minute trek through town. It was a long day to say the least, leaving one airbnb at 10am to arrive at our other at 330pm. If you’re new here, we have a 9 month old and a 2.5 year old. So it felt extra long to them, I’m sure. They actually did great though! That is, until my husband and I started discussing how they killed it and how lucky we were.. then, like clockwork, Izzy erupted with a gigantic meltdown. The best part was we were already in Lucca when she melted down. We literally had just gotten off the train and stepped into the elevator at the train station when she screamed the most horrific blood curdling scream ever. We legit thought the elevator door had ripped her little arm off and started to freak out ourselves. Both of us, wearing double backpacks, front and back (except my front was a 9 month old in a carrier), a stroller with a big ole diaper bag attached, a suitcase, and the frantic 2.5 year old were crammed into a shoebox elevator with zero room panicking and yelling and trying to figure out what the ef was going on. But don’t worry, her arm was fine.. we just forgot to let her push the elevator button. wtf. The meltdown did last awhile.. it mostly carried on during our 40 minute trek through town.. but it was a pretty big mistake on our end so who could blame her. Totally kidding.. toddlers are the worst. But it was a long day, she was totally out of routine, we were traveling through lunchtime and nap time and it was just too much for our little one. Definitely wasn’t fair, so even though she was a bit dramatic, it was totally understood.

Although it’s not always the perfect execution (is it ever with children?), we try to do a few things differently on travel days to make it easier on all of us. It mostly comes down to throwing expectations, limitations, and any kind of schedule out the window. And sometimes, no matter how hard you try and prepare, you fall short anyway. You just have to go with it.. put your head down, grit your teeth, and just keep moving forward.

Snacks

The biggest thing that always works for us is snacks. On a typical day we try to do healthier options and will limit quantity as to not impact their next meal. Travel days are different. You want 487 cheese poofs? You got it. Not our finest snack time, but those cheese poofs are currently acting as comfort food and their little world is upside down right now so.. choose your battles. Both our little ones feel much better with a snack in hand and that’s enough for us. We’ll even it out when we get where we’re going.

Screen Time

Another cringe. We bought our toddler headphones for this trip and I’m still side eyeing myself about it. That said, it’s been amazing having her content with her show on. She knows the headphones only come out on travel days and that adds to the novelty. It’s unlimited screen time when we’re dealing with planes, trains, and automobiles and she totally knows it. It gives her a sense of responsibility too since we tell her she’s in charge of making sure she has her own headphones with her at all times.

Stimulation

Such a no brainer, but easy to forget. Something new and different is always engaging. Even if it’s only for 5 minutes. Before our trip, I had packed Isabelle a big activity folder and didn’t let her see it until we boarded our flight. It had three small puzzles, a coloring book and crayons, stickers, etc. Separately, I stashed different stickers, action figures she had never seen, and coloring pads with the invisible marker (no mess!) Eventually we were circling back on activities and coloring pads, but the new aspect lasted well through our first week. I clearly held onto the goods as long as I could. Our current go to is “I spy” though and it’s quite effective.

Break up the Day

Pit stops, lunch breaks, transfers.. anything to break up the day and get them standing or walking. Not only can they stretch a bit and move their body, but the stop/change of scenery creates a bit of stimulation as well. A direct train or bus always sounds like the best option, but if you’re stuck on that form of transportation for an extended period, it could feel never-ending. We’ll always stay longer on a train since you can move around a bit and there’s usually a bathroom. A bus however, consider your options. Our bus ride yesterday was 20 minutes to Poggibonsi train station from San Gimignano.. it was short enough that neither kid was phased and I don’t think Izzy even had her headphones on. From there, we had two 1.5 hour train rides with a transfer in Florence. The transfer was short, but it at least got them off the train.

Sounds

Some people swear by using a sound machine on the go and I think it can really be a great tool. We’ve used ours on our stroller for our 9 month old, but not so much elsewhere. I’m very apprehensive to intrude on other people’s peace and space.. so I tend to stick to the less offensive and usually more tedious way of dealing with things. Bouncing and shushing is my go to unless our little became inconsolable.. then I think people would vote for a sound machine lol.

Timing

Obviously you are the only know who knows how to navigate this one, but it’s an important one to remember. Depending how we’re traveling that day will dictate when we’re heading out and if we’re squeezing in a nap beforehand or matching up our start time with naptime. Maggie will sleep in her carseat, but not so much in the carrier or our laps.. so if we’re planning a roadtrip, we usually plan to leave right at nap time so Mags will sleep during the ride. For trains and buses, we’ve been trying to squeeze in a nap before heading out. Even if we have to cut her nap short, we know she’ll be loads happier with having had a little rest beforehand.

The best way to totally prepare for a travel day though is to just lower your expectations. It’s going to be what it’s going to be and either way, you’re doing it and you deserve a pat on the back. It’s not easy and you already knew that when you decided to do it. So keep killing it and offering cheese poofs.

ONE MONTH IN ITALY WITH A BABY + A TODDLER

It’s been a minute since I traveled.. let alone wrote about it. To say it’s been a pretty crazy couple of years is a bit of an understatement. I’m not quite sure where all the time has gone and how it’s 2023 already. The last time I traveled internationally was January 2020 and it feels very strange even writing that. Obviously 2020 was weird and hard and devastating for most of the world, and when I remind myself that, I can’t really complain. But it was a dark time none the less. I started the year like everyone else, naive and so unprepared for what was to come. I had just found out I was pregnant and had a trip to Vienna with my best friend planned. The following month, February, I even had a 3 week backpacking trip with another friend worked out. Full itinerary and everything booked and set. China. Of all places to have booked for February 2020. I remember sitting watching the news days before I was scheduled to fly out, texting my friend and monitoring our flight. “Should we go?” “There’s no way this Coronavirus is going to be a big thing.. Can it?” I was a week outside the second trimester mark not only preparing to backpack through China, but about to embark into the epicenter of a virus that shut down the entire world. Obviously we ended up canceling. And then days after our initial flight plan, all flights to and from china were halted. I have no idea what our trip would’ve looked like if we had flown over there. Not to mention, again, I was pregnant. I did get to Vienna in January however. That was my last trip overseas and I suppose my first with Isabelle.

The rest of the year was an absolute disaster. But we did meet our little girl, so some good came out of it for us. We’re lucky. Cut to 2023.. we have two beautiful little ones (Marjorie *Maggie* joined us in 2022), we’ve updated quite a bit of our house, life feels really good, and now we’re looking at doing our first family trip abroad. I’d be lying if I said we’re totally pumped to bring a 9 month old and a 2.5 year old overseas, but we’re mostly excited. So there’s that lol. I’m focusing on the actual trip experience and I think that’s what is propelling me forward and motivating me to plan and brainstorm all the ideas and read all the things. Ben, I think, is focusing on the 8+ hour flight with two little ones, the actual getting to the airbnb with two little ones, moving around between cities with two little ones, and probably all the in between.. with two little ones. See the trend? There’s definitely loads to consider.. especially if you want to not only have an easy enjoyable time in general, but you also want your spouse to be up for another European vacation in the not too distant future, lol. So I have to make this look easy is what I’m saying.

TIME

The first thing we considered is time. How much time do we have to make this trip worth it. This question is different for everyone. I should actually preface with the fact that what worked for us may or may not work for you. I’m just sharing what helped us get into planning mode and made us feel a bit more confident (sorta?) to travel abroad with two little ones.

Now, we have time on our side for this trip. Ben’s job allows him to take a bonding leave for our second baby anytime within the first year of life. So we’ll be spending a month of his leave away. In my opinion, there’s nothing more bonding than long flights and uncomfortable train/bus rides. This time will either fly by or have us wishing we cut the trip in half. But for now, we’re super grateful for the time and hoping it’ll allow us to get to know a couple different cities and not feel rushed. I think time is the most important thing to consider when planning a trip with little kids. Especially if it’s your first big trip. You want to give yourself wiggle room for things to not go as planned. Or even just time and space to watch how your kid adapts and thrives in a different setting. I’m not suggesting taking an entire month to travel.. I know that’s not realistic. But “considering time” could simply translate to spending your vacation in one place. It’s mostly about not stretching yourself too thin and trying to cross too many things off your list. It’s also about considering jet lag and transportation once you get somewhere. Both of these cut into your time tremendously. Even though we’re spending a month traveling, we plan to land in Rome and stay in the city for three days. It’s not so much about seeing Rome as it is about getting ourselves and our kids into a bed as soon as possible. I have no idea how my kids will deal with jet lag.. it could be a day of misery and then totally fine for all I know. But three full days will allow us to recharge and rest a bit before continuing on. At the end of the day, you know your kid and if they’ll be pretty flexible and down to go with the flow or not. Having a toddler and a baby, this is our trip to test the water.

LOCATION

This sounds like an obvious one, but you’d be surprised. The more planning and reading I do, the more I want to throw a curveball into our itinerary. For example, will it be an absolute disaster bringing my kids to the Almalfi Coast? Probably not. Will it be super enjoyable bringing my kids to the Almalfi Coast with lots of cliffs, steps, cobblestone, etc? Again, probably not. And since this is our first trip it’s about setting ourselves up for success and not making things more challenging.. we’re trying to keep it simple. Our initial plan was Germany. We love it there, the people are always friendly, and if we’re shelling up with small kids, a place with good beer on tap sounds great! The more we tried to nail down cities and towns though, the more I was just overwhelmed and unsure what our actual days with the kids would look like. We wanted places we could hunker down for at least a week. We were hoping to get to know different towns and relax instead of being constantly on the move. We wanted to have a bit of breathing room, but be close enough to a downtown for essentials (and stimulation). A grocery store/market, park, a couple of restaurants, and a pub were on our list. There are so many cute German villages that hit all the marks and would leave us quite content. But something was just missing and neither Ben nor I were getting super pumped about the trip. It was almost like there were too many small towns to choose from and there was a hovering pressure to pick the right ones. I think we were both scared to park ourselves somewhere that maybe didn’t have enough going on and would leave us bored and feeling stuck. The key to choosing the right location for us came back to picturing what our actual days would look like with the kids. I wanted us to spend most of our time outside. Whether that was exploring, going for walks, hitting up the local playground, it didn’t matter. I just saw us out in sunshine. I started thinking about Italy mostly because it was more south and a bit warmer. From there, everything just seemed to fall into place. We were both pretty excited about it too, which was the biggest clue that it was the right decision for us. Not to mention, Italian food! Izzy is already telling people that she’s going on vacation to go eat pizza, lol.

When it came to narrowing down our itinerary, we knew we wanted to start in Siena. Benjamin has childhood memories of a summer in Siena when his Dad was teaching a law program at the University in town. He remembers spending his days eating gelato and heading into the market with his mother to gather fresh ingredients for dinner. His description of these memories are not only the most quintessential Tuscan experience, but also exactly what we wanted for our first family trip with the girls. This was pretty much everything we were picturing and the theme for finding places we wanted to visit. Big cities were out (with the exception of a couple days in Rome when we arrive and Milan when we depart) and quaint, pretty towns were in. Since we aren’t renting a car, we do have to rely on public transportation to get everywhere. This helped narrow down our search of not only ‘where to next’ but also, how long we want to spend on a bus or train between destinations. So keeping this mind, we started researching towns that could accommodate our vision, but didn’t have us sitting on public transit for too long of a stretch. Although absolutely stunning, we crossed out cliffside villages and places that have lots of stairs, hills, etc.. nothing is more annoying than carrying a stroller up a bunch of stairs.. except maybe a toddler screaming “I CAN DO IT” and taking all the time in the world to walk up themselves. That’s not to say we won’t visit these places at all.. it’s possible we may venture out to Cinque Terre for a day trip or something.. but knowing that we aren’t lugging all of our things and children up steps and hills and cliffs only to dread leaving the Airbnb with our little ones make all the difference.

OUR ITINERARY

So! After considering all the things, Italy is where we landed. Rome, Tuscany, Italian Riviera, Milan. We will be initially flying into Rome and staying 3 full days. Delta flies into FCO, but once the warmer months come around, flying standby in and out of FCO gets a bit difficult. Flights definitely do book up and last time I was in Italy I had to buy a ticket to Edinburgh, Scotland and then catch a flight home from there. I’m hoping that leaving in the beginning of May is early enough to get there without any issues. If not, that’ll be a whole other experience to be had with the kids. We can take our chances circling back to Rome and leaving out of FCO, but we figured since we’re heading North we could just continue on and leave out of Milan. After Rome, we’ll be heading to Siena for 8 days. Our Airbnb is right outside the city walls, but only a few minutes walk to the wall. There’s a yard for the kids to play in, a beautiful ivy covered pergola casting shade over the patio table, a grill set up, and a playground basically right across the street. From Siena, we head up to San Gimignano for 6 days. The medieval hilltop town is about an hour and a half outside Siena, which I think will be a nice and quick ride for the kids. And once we arrive in town, our Airbnb is only a 6 minute walk from the bus station. San Gimignano is one of the more well known Tuscan villages, but a lot of tourists tend to do day trips into the city. We’re hoping that staying there for 6 days will allow us to get a better feel for it. And to be perfectly honest, staying in Tuscany without a car I was a bit worried we wouldn’t get the full effect of the countryside view. I’m dying to see rolling green hills as far as the eye can see, cypress trees perfectly spaced apart stretching into the distance, rows of olive groves and vineyards layering the hills and just blowing my mind with their elegance. Well, San Gimignano delivers that. The medieval village is plopped right in the middle of exactly all that. The view from our Airbnb and obviously throughout the village is Tuscan landscape for miles and I cannot wait. Lucca is the next stop on our trip and we’ll be there for 5 days. Still considered Tuscany, Lucca can be found on every family friendly Italian city list. I’m still a little unsure what there is to do there.. everything I read really only talks about renting bikes and riding along the city walls.. but it looks cute, we like riding bikes, and it’s on the way to our next stop. Plus, it’s location also makes it a great spot to take day trips to Pisa and the beach. Not sure if that’s the plan just yet, but it’s nice having the option. From Lucca, we’re heading to the Italian Riviera and staying outside Genoa in a town called Sori. We’ll be there for 7 days. It’s only a 25 minute bus ride into the city, which will be nice being so close, but also much more relaxed and quiet. Our Airbnb has a nice sized outside space that is partly covered and overlooks the sea. This is where we spend the last stretch of our trip before heading up to Milan. We have 3 days in Milan, but will be traveling that first day and flying out the third. So it’s really only enough for the tiniest taste of the city before heading home.

ACCOMODATION

All of our accommodation is already booked for the entire month! We have 6 different places we’ll be staying and chose to do Airbnb for all of them. Airbnb has been hit or miss for us lately, but it made the most sense for this trip. We wanted an entire home for starters.. a full kitchen, living space, an outdoor balcony/terrace, and separate bedrooms. We want it to feel like our home away from home. We’ll probably be eating most breakfasts in our airbnb and cooking a lot of dinners as well. Both kids go to bed for the night between 7-8 and although we aren’t sticklers and know some nights will be later, we plan to stick to our normal routine for the most part. A balcony/terrace will allow us to put the kids to bed and sit out with a glass of wine or late dinner and still feel like we’re doing something out of the ordinary for us.. something that still feels special and like we’re on vacation. We’ve done plenty of road trips with Izzy and having an outside space has always been a game changer. Having separate bedrooms is huge for us too. Maggie will most likely be in our room, but we would like to keep Iz in her own room. She’ll be able to sleep uninterrupted and it won’t be too different than at home. Izzy has been sleeping in a twin bed recently so that allows us a bit of freedom in that we only need to request one crib for Mags. Initially we were thinking we’d have to take our travel crib, but decided against it. It narrows down the Airbnb search results needing a crib, but the luxury of not lugging extra stuff is so worth it to us. A few other obvious things we considered is where in town is it located.. we don’t plan on renting a car so we’ll be walking from the train/bus stations with all our bags and the kids. All our accommodation is within a 15 minute walk and we have some kind of idea what the walk entails.. hills, busy road, etc. For the exception of 2 of our stays, we made sure to have a washing machine as well. After living in Thailand for a bit, I’m no stranger to hand washing my clothes, but with two kids this will save us time and energy for sure. A couple other less obvious things we considered when picking our accommodation was lighting and decor. Before children, both of these were high on my list also.. but for different reasons, lol. As a parent, I’m considering lighting for nap time and decor is mostly about ‘less is more’ these days. I do love big windows and natural light does wonders for a space, but not so much in the bedrooms when my kids are trying to nap in the daytime. I found the cutest attic apartments in Genoa with gorgeous skylights and then remembered the children, lol. There would be no way for us to cover those windows. You won’t find many Airbnb listings that advertise black out curtains, but we managed to randomly find one, which was great! There are travel black out curtains you can buy and bring with you and also travel crib tents that block out light as well. I haven’t decided if we’ll be bringing any of these yet, but they are nice options to have. I’ve linked them below. I think we’ll assess closer to our departure date and decide. The less is more on decor is hard for me. I love a beautifully styled room and I’m definitely a sucker for plants and art and all things pretty. But I also don’t want to worry about my children touching or breaking things in someone else’s home.. Let alone helicoptering them to make sure they’re handling things with care. Lastly, if you’re in an apartment building check on the elevator situation. A lot of times in older buildings lifts only go up a couple floors and you have to walk 1-2 stories.. or sometimes there is no lift at all. A few of our Airbnbs are like this, which is fine.. I just like knowing what I’m walking into.

PACKING

We obviously haven’t done any packing yet. Dealing with a baby under 1 and a 2.5 year old, I can’t really let myself plan too far ahead. They develop so quickly that what they may be needing/wanting one month could be totally different the next. So for now, I’m doing as much reading and preparing as I can and then will assess my kids closer to when we’re leaving. I’ll be sure to post an updated summary of what we’re bringing when the time comes. That being said, Ben and I both plan on bringing our backpacking backpacks and a roller board suitcase.. our backpacks will be for us and the suitcases for the kids and all of their essentials. Also, as of now, we do plan on bringing a double stroller, a travel highchair for Mags, a fold up booster seat for Iz, no travel crib, and no car seats. We’ll be bringing a baby Bjorn carrier for Mags and possibly some sort of carrier for Izzy as well. Items that have been intriguing me however are: Tushbaby Hip Carrier, Travel Blackout Curtain with suctions for the window, Toddler Inflatable Bed for the flight over, and a Blackout crib tent for Maggie’s naps.

If you’re planning a trip to Italy, chances are, you’ve also been mentally preparing yourself for the few extra pounds you’ll be taking home with you. And who can blame you? One of the best parts of going to Italy is the eating and drinking! The first time I visited Italy, I had JUST finished the whole30 1 day prior. I was a little apprehensive about diving back into gluten and dairy- not to mention, sugar and alcohol, and actually thought I would continue to eat pretty clean while away on vacation. After all, my tastes had changed after 30 days and all I craved was healthy, nutritious food. So in my head, even though I was going to Italy, I wasn’t going to overindulge. WRONG. It was maybe 3 hours after landing and I was sampling ALL the pizza and buying blocks of cheese to take back to our Airbnb.. as snacks. As I’m writing this I’m feeling slightly embarrassed by my glutinous behavior, but also, a little turned on by the thought of so much cheese. I may have overdone it for sure, but to be honest, the only thing I learned from this was that the whole30 would just be better if pizza was allowed.

But anyway, back to food. We stayed in the Sant Ambrogio district and a handful of places on my list are in that area. Although we did quite bit of exploring and eating throughout the city, for some reason, our favorite spots were right near our Airbnb. It was a less touristy area, so I suppose that could be why.

I included 13 places on my list- all places we went to and loved- some specifically for the food, others for the location and/or experience as a whole. Florence really is a magical place to explore and eat, so I hope you have fun and your taste buds leave happy!

I macci

First on my list is I Macci! Situated in Sant Ambrogio Market Place, I Macci is a great spot for breakfast! Like most europeans, Italians don’t do big, eggy breakfasts like we do in the States. In Italy, it’s all about the espressos and croissants or biscuits. We stumbled upon I Macci one morning and were drawn in when we saw the spread of pastries and baked goods displayed on their bar and down the side of the restaurant. Everything looked absolutely gorgeous and the cafe was really cute and cozy inside. We assumed it was just a breakfast spot, so when we saw it was hopping in the evening as well, we were certainly surprised. Needless to say, we stopped back in for some wine and snagged a table outside among the many locals. The atmosphere here was super lively and hanging out in the crisp evening air in October with Italian wine was absolutely perfect!

panini semel

This was one of my favorites. I had read that this place was great for grabbing a sandwich and that was honestly enough to sell me on it. I love me a good sandwich. It only got better when I realized it was maybe a 3 minute walk from our Airbnb. DONE. We decided to stop by for lunch one day and actually almost walked right past it. It’s such a small shop! You step in, take one more giant step and you’re at the counter facing a cheery man asking you which panini and red or white wine. There’s a tiny counter half a step to the left with maybe 3 stools and that’s it. It’s very cozy to say the least. Obviously, the shop is more of a grab and go type place. We snagged the stools at the counter while we scarfed our sandwiches, washed them down with wine, and listened to the owner chatting with all his regulars that kept stopping in for their usual sandwich. It was awesome. And the sandwiches- freaking delicious!

malborghetto

Our favorite pizza! And we ate A LOT of pizza while in Florence. It’s what you’re suppose to do, I swear! Well, we were heading back to our Airbnb one night- it was maybe 10pm or something- and decided we should stop for a nightcap. Except instead of a cocktail of sorts, we opted for an entire nightcap pizza. (Did I mention the few extra pounds you go home with?) This was one of those places we kept passing and knowing we couldn’t leave Florence without seeing what it was about. We sat outside since they only had maybe 4 tables indoors, and patiently waited for our pie. Me with a glass of red, Ben with a Dolomiti beer. I can still taste the pizza to this day- perfectly doughy in all the right places and thin and cheesy OH MY GOD. I’ll never forget it. I hope you enjoy my attractive photo- it captures my feelings perfectly.

Hostaria Del Bricco

Across the river, you’ll find an area heavily populated with antique shops, artist studios, and cute little cafes and wine shops. Much quieter than the tourist heavy city center, but still full of life and thriving. It was late afternoon when we were wondering and exploring random roads and came across Hosteria Del Bricco. We were already thinking about dinner and what we should do and something just felt right about this place. I have to give Ben all the credit on this one because he was the one that was totally drawn to it. They weren’t even open for dinner yet and he was in the window scoping it out. The owner came by at the right time and let us look at a menu. There it was! Bistecca Alla Fiorentina- Florentine T-bone steak. This is one of their traditional, Florentine meals that you must try when in town. We were sold and luckily, they were able to squeeze us in between reservations! We popped over to the wine bar a couple doors down, shared a burrata with some wine and waited for our dinner reservation. It DID NOT disappoint. The experience as a whole was wonderful and I’m still so happy Ben found it!

grom

GELATOOOO. Located right near the Duomo, Grom is the perfect place to stop for a gelato while you wander the streets. Their pistachio is dynamite, but I couldn’t just do one- so I went for pistachio andddd coffee on a cone. Absolute heaven. Ben went salted caramel in a cup and savored his wayyy longer than I did. There are loads of places to grab a gelato, but there’s definitely a reason why Grom is more well known!

santarpia

Another victim of our late night pizza stops, Santarpia is located right across from I Macci in the Market Place and serves up Neopolitan pizzas with unique topping combinations. We didn’t get too wild here, but we did opt for yellow heirloom tomatoes and smoked mozzarella and it was absolutely delicious! I’ve since read that Giovanni Santarpia, the pizza genius behind Santarpia left the restaurant this past summer. So unfortunately, I have no idea if these gourmet pies are still top notch, but I do think it’s worth scoping out!

trattoria mario

If the thought of being crammed in next to strangers in a hectic environment doesn’t scare you away, keep reading. This place doesn’t look like anything special- no-frills for sure, but it’s also an institution in Florence. Authentic Tuscan food with reasonable prices keep the crowds coming back for more! Most likely, you will have to wait for a table, but it’s worth it for the experience. We ended up ordering a random smorgasbord of food, including soup, pasta, and even a steak and it was all delicious! You will probably find this place on other various blogs and lists of where to eat in Florence as well- it truly is an experience.

Mercato Centrale

Quick and casual! Mercato Centrale is located in the San Lorenzo Market area, making it a great place to stop for a snack or a pick me up! Before heading inside, check out the outdoor market itself and do a little shopping. It consists of stalls selling leather bags, pottery, clothing, and various souvenirs- so make sure to explore! Once you step inside, into Mercato Centrale, it’s all about the food though! Specialty shops, fruit and vegetable vendors, cheesemongers, wine stalls(!!), and butchers fill the entire space- it’s like if you were to place Mario Batali’s Eataly actually IN ITALY- but better, cause ITALY! Basically, it’s just magical. Load up on truffle oil or balsamic glaze to take home with you and then pick a place to order some food! You really can’t go wrong with a charcuterie board or cheese plate! Wash it down with a glass of wine and you’re ready to take on the rest of the day!

mayday club

Located down a small, quiet lane, Mayday Club is a great place to stop and grab a drink! All kinds of funky decor plaster the walls and create a fun space to hang out and sip on craft cocktails. The menu is extensive and unique and their garnishes are on point! I mean, a strip of bacon was placed over my martini rim and it was an absolute perfect accompaniment! And any place that has free popcorn is a gem in my book! It’s cash only- so make sure to stop at the ATM.

Osteria Il gatto e la volpe

This place is perfect to keep in your back pocket if you’ve spent the day doing all the touristy must dos and are exhausted and starved. Located riiiight around the corner from The Bargello, Osteria Il Gatto E La Volpe serves up pizza and pasta that will satisfy your needs. We ordered a couple of pasta dishes and sipped on delicious house wine and it was perfect after a long day of museums and sight seeing. I do have to emphasize the location being really prime here. Finding a good restaurant in a tourist zone is tough sometimes and if you don’t have the energy to leave the area, this is your place!

entecA alla sosta dei papi

One of the coolest spots to drink wine and just hang out! A glass of house wine- and by the way, you can never go wrong with house wine when in Italy- will cost you 3 Euros and it comes with a few crostini. Seats inside are limited, BUT! just take your wine and little plate of snacks outside and sit in the road. Seriously. Enteca Alla Sosta Dei Papi is located on a quiet side street so everyone just hangs out in the street! There are a couple tables outside, but mostly, people stand or just sit on the ground. It’s definitely a place for locals and maybe why we loved it so much!

Locale

This is the place to either go and splurge orr simply grab a cocktail and dessert. (A cocktail can run you 25 Euros- but the atmosphere is worth it!) Located inside the enchanting Concini Palace, Locale Firenze is an incredible setting. You walk into the dimly lit space and are immediately struck with a gorgeous bar of glowing backlit liquor bottles and living walls of foliage. The ceiling is completely glass and emphasizes the modern touches without overtaking the medieval qualities that is the Concini Palace. The building itself has been around since the 1200s and during the 1500s, was tied to Florentine politics and the Medici family. Before you head out, ask a Locale employee to give you a quick tour of the basement- this is the best part! Check out the original rooms that existed 800 years ago and see where they kept all their wine.

il pizzaiuolo

MORE PIZZA. I know you must be wondering how much pizza we actually ate on this trip and all I can say is that, it really is no one’s business but our own, hehe. But I also may have just lost track myself. Il Pizzaiuolo was one of the first places we went. It wasn’t a late night stop like the others..*uncomfortably looks down at the ground* We actually went for dinner and had to wait a bit to be seated. And the entire time we dined, there were people waiting for tables. The restaurant was cozy and warm all while having a distinct, busy, fast paced, Italian pizzeria atmosphere. The menu had more than pizza on it, but I don’t think I saw anyone eating anything BUT pizza. And rightly so- it was absolutely delicious!

The amount of restaurants in Florence is absolutely insane and I encourage you to go with your gut when wandering and finding new spots. We love doing our research and having lists of places to try, but we also always incorporate places we find on our own as well. And sometimes we like them best :) So explore and have fun! And don’t worry about eating too much- it’s Italy!

Art in Florence. While incredibly romantic and inspiring, it can also be a bit daunting. The amount of paintings, sculptures, and architecture residing in this small Italian city is completely mind blowing. And seeing it all is just not possible. The Uffizi Gallery in Florence is the most prominent (and largest) art museum in the city and chances are, you already have it on your list of places to go. However, just because this museum is the largest and holds an incredible collection of Italian Renaissance work, it does not have everything you may be hoping to see. For example, Michelangelo’s David is located at the Accademia across town, while Donatello’s David resides in the Bargello. Other important sculptures and countless paintings are also scattered throughout town in various locations, from public squares to cathedrals and churches. So although the Uffizi Gallery is a must, keep in mind that you may be hopping around to other museums and/or locations to see certain works.

With this in mind, I put together a list of Uffizi highlights to help you narrow down your list and save some time. That being said, if time is on your side, I encourage you to spend a leisurely day exploring the halls of the Uffizi and really taking in the inspiration around you. Being an Art History major, I hate suggesting you skate over certain time periods or artists, but I also just understand not having enough hours in the day to fit everything in.

The highlights I included below are not in order of importance, but rather, in the order I came across them in the Uffizi. They should still be in the same locations :)

Santa Trinita Maestà- Cimabue- 1280-1290

Created between 1280-1290 by the artist Cimabue, the Santa Trinita Maestà was created for the main alter of the Church of Santa Trinita. The significance of this piece and why I included it in my list is its Byzantine style. The abundance of gold and lack of perspective in paintings were typical to these times. Not only did Byzantine art consist of religious icons, but it also reflected a lack of realism. Starting your Uffizi highlights with Cimabue’s Santa Trinita Maestà, you’ll be able to see just how much style evolves over time.

Ognissanti Madonna- Giotto-1306

Located in the same room, you will find Giotto’s Ognissanti Madonna. Again, like Cimabue’s work, this was painted for an alterpiece in Florence and reflects a similar time period and composition. However, this piece showcases more modern qualities. Two things to note- the layout of the surrounding figures and the Madonna’s weighted form. The layered aspect of Giotto’s surrounding figures creates dimension and is more realistic than Cimabue’s stacked heads. Additionally, the Madonna’s robe drapes between her knees and off her breasts alluding to the fact that she does actually have a body. The realism here is something not typically seen and suggests the initial shift and advancement in Italian art.

The Duke and Duchess of Urbino- Piero della Francesca- 1473-1475

Created as diptych, these traditional portrait style works show the Duke of Urbino, Federico da Montefeltro and his wife Battista Sforza sitting in profile facing each other. The rolling hills and vast countryside of their property stretch out behind them and emphasize their significance. What’s noteworthy here is the use of perspective. The hills reach into the distance not only becoming smaller and smaller, but also, the colors becomes less vibrant and more faint.

Cestello Annunciation- Sandro Botticelli-1489-1490

Although Cestello Annunciation is the least famous of the three Botticelli works I included in this list, it is absolutely worth checking out! The Annunciation was and continues to be popular subject matter for religious art. In fact, many well known artists from the Italian Renaissance, including Fra Angelico, Titian, Filippo Lippi, Da Vinci, and countless others created their own versions of the Annunciation as well. The sheer veil worn by the angel here is one of my favorite details that’s easy to skip right over. The delicate quality is mirrored by both figure’s raised hands and elongated yet dainty fingers. Dimension and perspective is used by the tiles on the floor as they shorten in size and the landscape continues into the distance.

La Primavera-Sandro Botticelli-1477-1482

Also referred to as Allegory of Spring because of its many allegorical meanings, La Primavera is one of Botticelli’s most well known works. It was created for a member of the Medici family and thought to symbolize Renaissance Humanism and Neoplatonic ideals. Most critics believe it is an allegory of Spring however, hence the nickname. The painting is read from right to left, with the blue figure, Zephyr creating growth by impregnating the nymph Chloris. Chloris in turn, transforms into Flora, symbolizing Spring and scattering flowers on the ground. In the center, we find Venus presiding over the event, while the Three Graces dance together merrily, and Mercury, the figure to the left, chases the remaining clouds away. Cool fact- there are over 300 different plants depicted throughout the work.

Birth of Venus- Sandro Botticelli-1485

Birth of Venus is Botticelli’s most famous work and will most likely have a crowd swarming around it. Venus stands front and center on a seashell, almost appearing to be presented to the viewer. It’s absolutely striking. The painting lacks perspectival elements like we’ve seen in other works thus far, but the classical subject matter and stylized Venus is enough to capture your attention and draw you in.

Laocoön and His Sons- Baccio Bandinelli

The Laocoön and His Sons in the Uffizi is a copy of the Hellenistic original which is located in the Vatican. Bandinelli was commissioned in 1520 by Pope Leo X de’ Medici. He is said to have used 3 blocks of marble, contrasting the original which had been carved from a single block. The sculpture is super intricate and relays the sense of agony and struggle while the figures strain to free themselves and fight to survive.

The Baptism of Christ- Andrea del Verrocchio + Leonardo da Vinci-1474-1475

In 15th century studios, it was typical for artists to design a piece and have apprentices or students work on it. This was the case for The Baptism of Christ. The artist, Verrocchio was a master painter and apprenticing under him, was Leonardo da Vinci. Da Vinci began his apprenticing at a young age and was heavily influenced by Verrocchio’s work. In The Baptism of Christ, Leonardo was responsible for the angel on the left and a part of the background above. Looking at the angel’s face, you can see characteristics of Leonardo’s style.

Annunciation by Leonardo da Vinci-1472

Annunciation is one of Leonardo’s earliest major works and was created in Verrocchio’s workshop. It is also said to possibly be a work of collaboration. The painting depicts the religious scene in a nature setting and with atmospheric elements that later become characteristic of da Vinci’s work. It’s an interesting piece. Contrasting other Annunciation paintings that depict a more serene setting, this shows an angel appearing with tense, almost aggressive wings and a Mary that seems to be pulling back and unsure.

Judith Slaying Holofernes- Artemisia Gentileschi-1620

By far, one of my favorite works. EVER. I’ve been fortunate to not only see this work in Florence, but also in Chicago when we had her on loan for a short time. The story depicted here is taken from the Old Testament and is when Judith kills the Assyrian general Holofernes, freeing the Israeli people from Nebuchadnezzar's army. This piece is the only painting on my list done by a woman and the fact that it depicts a woman beheading a man is just mind blowing. What makes it so much more impactful is that Artemisia is said to have painted herself as Judith and her mentor, who had been tried and convicted of her rape, as Holofernes.

Medusa- Caravaggio-1597

As the story goes in Greek Mythology, Medusa was a Gorgon monster whose hair was made of living, venomous snakes. Just by looking her in the eye, you would immediately be turned to stone. Commissioned as a ceremonial shield, Caravaggio modeled himself for Medusa’s face. Ohh, the irony of modeling yourself for a character who turned people to stone by looking them in the eye. (Get it? He was staring at himself.. Okay.. maybe it’s not that funny). But anyway, the painting depicts the moment that Perseus beheads Medusa and a look of shock overtakes her face. The shield itself was actually a convex surface and Caravaggio somehow tricks the eye to making it look concave.

As I mentioned before, there really is so much so see and take in at the Uffizi. These are just a few highlights if you’re short on time and can’t spend your entire day meandering the halls. Don’t forget to get over to the Accademia and the Bargello as well! I will also be adding a post on a Free Self Guided Walking Tour in Florence anddd a Top 10 Absolute Must See Works of Art! So stay tuned :)