Our Italy Itinerary (with a toddler)

We got back last night from a two-week trip to Italy with a two-year old! Some warned us against bringing a toddler and kindly said “leave him with your parents,” but for such a long trip, we really wanted to stick together as a family and make these memories all together. We had an Italy trip planned for March 2020, wich got cancelled due to covid, so we were thrilled to finally be able to make this happen!

Here is everything we did on our trip!

Rome

We spent our first four nights in Rome at the Grand Hotel del Gianicolo and absolutely loved this hotel. It’s tucked away in the beautiful and historic Trastavere neighborhood in Rome- a bit quieter and away from the hustle and bustle, but still easy to walk everywhere. The service, the breakfast, and the accommodations were delightful. They even had a pool, which was wonderful for the early September 86º sunshine. This was my favorite hotel we stayed at on our trip! Here is everything we did and loved:

• Day 1: Walked to Fontana dell’Acqua Poala, Vittoriano, stopped for incredible pizza at Pizza Florida, then along Via Dei Fori Imperiali (amazing views of ancient ruins, historial architecture and monuments) to our Colosseum, Forum, and Palatine Hill guided tour. Had Rome’s famous homemade carbonara for dinner at a family restaurant.
• Day 2:Vatican City: St. Peter’s Basillica, the Vatican Museum and Sistine Chapel (A few notes- there are a lot of people outside the basillica entrance tryint to sell you tickets, but entrance to the basillica is free and although the line was long, it only took about 30 minutes for us to get in. The museum is ticketed, but it includes entrance to the Sistine Chapel. We bought our tickets online and were able to skip a massive line of people waiting outside. Vatican City was very crowded, but absolutely worth it- this was one of my favorite days of the whole trip. If you can, go in the morning.) After the Vatican, our golf cart tour guide picked us up (you can book through this number: +39 351 4782849) – this was one of my favorite things we did! We learned so much and this is one of the best ways to see the whole city in just a few hours. Book it at sunset time if you can- the views are insane!
• Day 3: Swam in the morning at our hotel, visited the Pantheon (wow, it’s worth going inside) and had an amazing, slow dinner (Charlie was asleep in the stroller) right next door at Hostaria Pantheon. Walked to the Castel Sant’Angelo (super interesting history here about the Pope fleeing the Vatican for safety), then tool a stroll along the Tiber River north to Campo Marizio, a shopping area in Rome. Ended the evening at one of Rome’s most famous gelato spots, Gelateria Frigidarium.
• If you walk by a church, peak in! Every church is beautiful inside and worth seeing. I feel the same way about all the food we ate- you really can’t go wrong. Everything we ate was amazing. Bring comfortable walking shoes…we walked a ton!

Venice

We stayed at the Hilton Molino Stucky Venice for the next four nights, and although it was a beautiful hotel and very comfortable for a family, I don’t think I’d stay here again. It felt too American, too corporate, and we couldn’t even get a decent round of morning coffees without spending €25. We booked this hotel mostly for the rooftop pool, but the pool was closed 2 of the 4 days we stayed there. We also had to take a water taxi to-and-from the hotel into Venice, and sometimes the boat was full, which left us waiting for about an hour to get back at night. It did not have the quaint, authentic Italian feel of our first hotel, and for that reason I don’t recommend staying here. If I could go back, I’d opt for booking an Airbnb in Venice proper from a local. One more quick note on Venice- we learned quickly that it is not stroller-friendly at all! After the first day, we ditched the stroller altogether as it was too difficult to carry it up and down all the bridges with stairs.

• Day 4: high speed train from Rome to Venice (about four hours), a beautiful sunset dinner at Ristorante Riviera (10/10)
• Day 5: wandered around the iconic streets of Venice and watched boat races and a boat parade. Pastries, fresh juice and cappuccinos around town, and ended the day in the beautiful St. Mark’s Square at sunset. Charlie chased pigeons for what must have been an hour with other toddlers from all over the world.
• Day 6: Doge’s Palace tour, a gondola ride with a 5th-generation gondolier, and a classic Venetian-style dinner (amazing risotto!)
• Day 7: St. Mark’s Basilica tour and a cozy, rainy night ordering room service and watching Merchant of Venice in bed

Florence

Our last stop was at the FH55 Grand Hotel Mediterraneo. The service and the breakfasts were wonderful, but I probably wouldn’t recommend staying here as it wasn’t as clean as I would have liked. It was right along the Arno River, which we liked.

• Day 8: High speed train from Venice to Florence, dinner at Osteria Cancello Dei Macci for the famous Florentine t-bone steak (this is a five-star restaurant without being fussy- they were incredibly warm and welcoming to Charlie and we even chatted with other people eating here. A real local vibe with authentic food. Probably my top recommendation for food from this whole trip.)
• Day 9: Florence walking tour and Galleria dell’Accademia (booked through CiaoFlorence). The statue of David gave me chills and is truly mind-blowing. You can see some of Michelangelo’s half-finished works here too, which I found fascinating. From there, we had sandwiches at Florence’s most famous sandwich shop, All’Antico Vinaio. Worth the wait! A visit inside the Duomo made for the perfrect ending to our first day in Florence.
• Day 10: We headed up to Piazzale Michelangelo for views of the city, with stops at the fountains along the way. Boboli Gardens was one of my favorite things in Florence. No crowds- just breathtaking views of the hills and the city. Charlie made friends with the locals.
• Day 11: Semi-private wine tasting tour (also booked through CiaoFlorence) through the hills of Tuscany. We had the BEST tour guide and an incredible dinner in the vineyard. It was great to have at least one day of our trip in the countryside after being in cities the whole time (would have loved to do more of this- next time!)
• Day 12: Train back to Rome with amazing pizza, hotel swim and free appetizers, and a conked-out baby. We stayed at the Hilton Rome at the airport which has a pass to walk directly to the terminal for our early-morning flight the next day.

A few stereotypes about Italy and my thoughts:

1. People really do dress up more in Italy! I think there are a few reasons for this; one being that most of the basilicas/religious sites enforce a strict dress code. Also, when visiting such incredible, breath-taking sites, it shows respect for history and the beauty of the place by dressing nicely. I could have ditched one or two of the pants I brought and swapped for one or two more nice dresses/skirts, as I ended up just wearing my skirts on repeat.
2. The food really is better in Italy! Everyone talks about how amazing the food is, and they aren’t wrong. Pizza from a casual spot at the train station was one of the best slices I’ve had in my life. You really can’t go wrong with anything. I’d just recommend avoiding places with laminated menus with pictures- go for restaurants with their menus in Italian first and English second, locals eating inside, and one street back from the main tourist streets. White tableclothes are also a good sign.
3. Italians love kids!!! Many people told me this before we left, but I was still pleasantly suprised by how warm and friendly the Italians were to Charlie. He got so many head pats, high fives, and knuckles from random strangers. A waitress in Florence picked him up and carried him around the entire restaurant to greet everyone. Musicians in Venice let him come say hi and play their instruments. We even had a chef at one place prepare his food and serve him before even taking our order. At every line at the airport, they let us skip ahead. A group of local teenagers played, coloured, and talked with Charlie for over an hour. Nobody made us feel like he was an inconvenience- and this was a big highlight for us!