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.