We took our 3 kids (13, 11 and 8) to Italy for 2 weeks this winter from Dec 28-Jan 11. They’ve never been outside of North America (at least since they were toddlers) so this was their first trip of this type.  It was an amazing experience with lots of interesting things to see on the way, great food, and pretty good weather (compared to where we came from). I’ll share some things we learned and suggestions if you decide you want to travel there as well. There are some links in here but they’re not specific endorsements from me and I get nothing for you clicking them, so use as you see fit.

We flew to Rome then took trains to Naples, Florence, Venice, and then back to Rome. Each of the trains was a high-speed one with FrecciaRossa and varied in length from about 1.5 to 4 hours. The trains were excellent and it was SO much better than flights for getting to/from the station, getting on/off the train, etc.

We went during the winter which meant there were no hot days but it got up to around 10-15 degrees Celcius as a high each day. Some rain off and on but mostly pretty nice. It meant you could walk around for any length of time and never get hot, like you would in the spring/summer/fall.

Here are a bunch of random suggestions and lessons learned on the trip that might be useful to you:

• Traveling to a place like Italy in the winter is great. You don’t get the beaches and suntans, but you can still eat outside (with heaters at most spots), crowds are much smaller than during high-season (which is especially great with kids) and you can walk for hours without getting hot or needing constant water to drink.
• Eat outside when you can! This is a big part of the experience of being in Europe for non-Europeans. It’s a great way to point out things, people, etc. going on for kids and it feels more natural to have conversations as a family. It’s a big thing, even in the winter and I was very pleasantly surprised to see how doable this is.
• “Breakfast included” is a big deal. Most Italians just have a croissant and coffee for breakfast which doesn’t work for all kids and is pretty low on vitamins and protein. If a hotel includes breakfast, you can be sure there will be eggs, fruit, toast, cheese, meats (as well as many pastries) to eat. For kids especially, having cereal, yogurt, fruit available, can be helpful. We had breakfast included about 1/3 of our time but it was great when we had it. Next time, I would probably prioritize this higher when looking for places to stay.
• Toilets are very hit-and-miss. Most (including the women’s toilets) don’t have toilet seats which was not fun for our daughter especially, although we still used them many times. Count on pay toilets in the train stations and similar spots (usually 1 Eur) and subpar toilets in most restaurants and other areas. Best to use the hotel ones, which are always good, and even feel free to go into the lobby of a hotel to use theirs. Especially for kids, they are very unlikely to stop you and those are always better than the restaurant ones. Bathrooms on the train are small but fine – usually better than the restaurant ones and free, unlikely the ones in the train stations.
• Pickpocketing remains a big risk that many people brought up for us so we came prepared. Protect your phone or wallet by either using a shoulder bag (which my wife and son did) or a zipper-pocket (which I did with the pants I brought with me). These ones have a back zipper pocket but I’m sure you can get some cheaper ones too.
• Rome:
  • Spanish steps are packed by late morning. Go at 8am and there’s essentially no one there. We had it all to ourselves and got our best pictures and views at that time.
  • “Welcome to Rome” show is a nice way to get settled and give a brief history for kids. The side shows are a bit dry for kids but the main film is about 25 minutes and went over well with the whole family.
  • The Vatican and the Colosseum are both great but quite large and can be less exciting for kids without the right tour. We used “Rome Tours with Kids” which tailored the tours to our kids ages and made both of them quite successful. Highly recommend going with tours that are small and aimed at the right age group.
  • Stadio Olimpico is great if you’re able to see a football/soccer game. We same the two Rome teams (Roma and Lazio) play each other which was especially exciting but it’s an experience to be there regardless. Buying tickets can be a bit confusing but we just used StubHub and got some really good seats the morning of the game.
• Naples:
  • Buy a Napoli scarf (for their football/soccer team) and everyone will be your friend. You can buy them at many souvenir shops or road-side stands. Our son did this and he enjoyed all the positive comments and cheers as we walked around. A fun thing for a kid to do. Note that you can do this in Venice (Venezia), Florence (Firenze) and Rome (Roma/Lazio) as well. Rome is a bit trickier since there are supporters for both teams but people responded with good-humoured jabs if they supported the other team.
  • Naples Underground Sotteranea tour was good, but do the English one not the Italian one (like we did). Lots of talking so if you don’t understand it, the first half can be boring for the kids. They still loved going through the tight, dark tunnels though so it’s worth it regardless.
  • Pompei is huge. Well worth going but need a good guide. Suggest again “Rome Tours with Kids” (which we used multiple times) to tailor the tour to the age of your kids. You don’t need to see all of it to enjoy yourselves. Our kids loved it. The ride is ~25 minutes each way but the tour groups will help with transportation to/from your hotel if needed.
  • Do a walking tour. The old town area is great but it’s chaotic and confusing. We did a pastry tour via “WithLocals” where you walk around, learn about the area, get good advice on what to do and stop for 3 pastries and 1 gelato over the course of about 2.5 hours. This was a great way to get to know the areas that we came back to multiple times after this. There are also food and drink tours, but we did pastries, which I don’t regret.
  • Old town is chaotic but interesting. We ate at Monsu which is a basement place on a side-street.  They had great food and were never busy. Our favourite pizza was at Pizzeria Attanasio in the old town area. Try the anchovy pizza if you’re feeling adventurous.
  • New Year’s in Naples is NUTS(!) We were there at that time and fireworks are going off right in the streets from mid-afternoon on. It was loud, chaotic, but quite interesting. At midnight, it’s a 30 minute non-stop fireworks explosion so even if you’re trying to sleep everyone will wake up for at least that length of time. It can be a fun time but don’t count on getting much sleep that night and you want to navigate it carefully with kids.
• Florence
  • One of the unique highlights for me was the “Wine door” on Osteria Belle Donne. You can just walk up, knock on the door, order wine, and they sell it to you to take away. It’s just a gimmick but I found it very satisfying and it gave the kids lots of talk about.
  • Accademia Gallery – Go straight to the room to see David first. You can go back through the musical instruments area (which was great!) and some of the others after, but the David room fills up so skip past the other parts first and go there. Book your tickets before and get there when they open at 8:15 and the room will be almost completely empty. Later in the day, it can be a 1 hour+ wait to see David, which is probably not worth it for kids. But first thing in the morning, you can walk right up and get time to look at it, take pictures, talk about it, etc. Well worth it. It’s a pretty small museum besides David so you can get through the rest in under 1.5 hours.
  • Book the Duomo climb at least a week in advance. We looked a couple of days before and there were no times left. You can still get into the cathedral for free(!) and pay to climb the tower, which is great, but the Duomo climb is the hardest to get. The cathedral has pretty bare walls (despite looking very impressive from outside) but the dome inside is very nice and so is the clock, so it’s worth a visit.
  • Look ahead for Pisa tours as well. It’s an easy 1-hour train ride each way. Again, we missed our opportunity to do the climb, so we didn’t bother going over. I think it would be a fun thing to do with kids but I remember Pisa being low on other highlights when I last visited, so without the climb, it might not be worth it.
  • Il Latini has a great “family meal” which is a multi-course meal that everyone at the table needs to go for. It’s 3 hours long but lots of nice things to try that are pretty kid-friendly, as long as they’re willing to eat steak (which is the main meal). This was our biggest, longest meal but everyone liked it. Reserve the first time slot at 7:30 and start lining up 15 minutes early. Lots of people will show up and they’re all trying to get in at the same time. Be near the front of the line if you can.
• Venice
  • Rolling suitcases are a pain everywhere in Italy, but especially so in Venice. There are lots of bridges that have several stairs up and down and we often watched people struggling to get across the bridges. We brought backpacks for all of us and even though they were a bit heavy at times, it was much easier to get to our hotel from the train station (and back).
  • Don’t use the ATMs in Venice! The exchange rates are poor and they charge a 15%(!) surcharge on withdrawals, on top of your bank’s fees. You will likely want some cash in Euros for things like the Gondolas, so take cash out at a bank in another city (not a random ATM, but only one directly connected to a bank) before getting to Venice or bring cash with you from home. You don’t need a lot, but you’ll need some.
  • The gondola ride is 90 EUR which isn’t cheap but is a nice experience for the family. Don’t expect singing or any talking at all from the gondolier, but it’s still a nice experience. Great chance to take good photos and one of those things you’ll probably regret if you don’t do it. You can book these in advance online but it’s more expensive. Suggest you just have 90 EUR with you and go to a quieter area to catch one, instead of going to the main gondola hubs.
  • The DaVinci museum is quite fun for kids. Just reading and looking at things on the main floor but once you go upstairs you get to see and play with models of several of his inventions. Lots of interesting stuff and the ability for kids to try some of them directly. We all enjoyed this.
  • Venice water bus is a nice way to get to/from Murano which is worth a visit. The quickest route is from Pte Nueva to Murano Colonna which is only about 10 minutes. You can get on/off at other stops as well but all the other routes are longer. You can buy tickets right at the stop before getting on. It can get a bit expensive for families of 4+ but it’s cheaper than any other options. This site has the best up-to-date schedules and was very reliable for us: https://m.chebateo.it
  • If you do go to Murano, we liked the glass blowing demonstration at the Glass Cathedral (Santa Ciara) which is ~10 Eur per adult and cheaper/free for kids. Just a 5 minute walk from the water bus stop, on the other side of the bridge.

Overall, this was a great experience that our whole family enjoyed. Lots of memories and stories for them to tell. It’s getting everyone excited for our next trip which is exactly the take-away we were hoping for.