We’re recently back from our two week trip to Italy over winter break, still full from daily doses of pasta, pizza and gelato it was the longest trip we’ve been away together as a family of five, and one of our most favorite adventures. I always have a hard time finding solid recommendations when we’re traveling with the kids that don’t feel like paid advertisements so wanted to share some of our favorite places, restaurants and general tips for planning and organizing the trip.

Hands down, the best part of the trip was getting to experience the country through the eyes of our three kids – now ages 12, 9 and 3. Our 9 year old begged us to take her to the Leaning Tower of Pisa, a tourist attraction we never would have prioritized but the day trip from Florence – spending 10 mins at the Leaning Tower and then the rest of the afternoon eating and shopping in the nearby town of Lucca was one of our unexpected highlights. Shopping for perfume with my 12 year old daughter (who like most every girl I know her age has a skincare obsession) in Florence at Aqua Flor and Santa Maria Novella was such a fun and special experience. And it didn’t take much to delight our 3 year old who was just as excited about riding a carousel in Florence as he was by watching construction vehicles dig up the new subway in Rome.  

My friend Lauren who works as a travel agent for Smart Flyer was incredibly helpful in selecting our hotels, would highly recommend her for booking travel especially with kids. I organized and booked all the other reservations on my own with the help of the hotel concierges. I’ve my recommendations below by city and tried to include hotels, food and activities but feel free to reach out with any questions!

Pre-trip and overall planning

We picked Rome as a destination because there is a direct flight on Delta (where we have all our miles) from New York City – but knew we wanted to combine it with visiting at least one other place. We had heard wonderful things about Castiglion Del Bosco, a Rosewood Resort in Tuscany in between Rome and Florence. It did not disappoint and ended up being a highlight of our trip. Our daughters were really excited about Florence and it seemed like an easy enough trip from Rome – we took the overnight flight, landed in Rome in the morning and hopped on the train from the airport directly to Florence. I thought it would be better to book the train tickets ahead, but in hindsight it would have been much easier to just purchase them at the kiosk at the airport in Rome. You need to take a train first from the airport to the city center and then just transfer to the fast train to Florence which takes about 1.5 hours. It was all pretty easy considering we had just landed form an overnight flight and were schlepping two weeks worth of luggage. We decided to spend four nights in each location which was the perfect amount of time to see each place and really make the most of being at Catiglion Del Bosco.

Florence Recommendations:

Where we stayed:

Hotel Lungarno – we LOVED this hotel and would definitely recommend it. The location was great, it is literally on top of the Arno, just on the other side of the bridge from the Uffizi Gallery. It felt a little quieter staying on this side of the river, we had a large family suite overlooking the water with our own balcony connected to another double room for the girls. The setup was ideal for the five of us and the staff at the hotel were so nice in helping arrange a babysitter in advance and also a last minute rental car to Pisa. 

What we did:

The only experience I booked ahead in Florence was a three hour walking tour of the city that included a brief visit to the Uffizi. The kids were a little bored by the museum but I think they appreciated the overall tour – Florence is a pretty easy city to navigate and explore in two days or so. 

I would definitely recommend a visit to the Synagogue in Florence, it’s absolutely breathtaking – there is a small museum inside which gives you some of the history of the building and the Jewish community in the city. 

I heard the Church of San Lorenzo just opened access to see Michaelangelo’s original drawings alongside the tombs of Lorenzo de’ Medici. We couldn’t get tickets but that’s something else to check out.

Shopping at Aqua Flor with the girls was definitely a highlight, you can book a perfume experience ahead of time where they take you down to the laboratory and you can actually create your own scents but it’s expensive and there was more than enough to sample. 

Santa Maria Novella was also fun to visit, one of the oldest pharmacies in an old church which itself is worth walking into see – I personally preferred the products at Aqua Flor, so did my daughters. 

I stumbled upon a little shop selling the most beautiful textiles – Lisa Corti is based in Milan but has a store in Florence and Rome. Her block prints are all designed in Italy and crafted in India, I brought home a table cloth I am in love with. 

We ended up renting a car through our hotel and driving about 40 minutes to the town of Pisa. I’m actually kind of glad we saw it, our daughter was delighted and thought it was super cool. We literally walked around the building and grounds for 10 minutes, took some photos and then kept driving to Lucca which is a beautiful small town about 30 minutes away. It reminded me of a smaller version of Sienna, it’s known for the old stone wall enclosing the city center. It was beautiful to just meander around the cobblestone streets, do some shopping and is known for good restaurants as well.

Food Recommendations:

Ate at Il Santo Bevitore – about a 5 min walk from our hotel, loved this restaurant we went for lunch without reservations and it was delicious. I got the sense you need to book ahead, we definitely would have come back for dinner. 

13 Gobbi was our favorite dinner in Florence. It’s a pretty traditional trattoria and was full of locals, we had a reservation ahead and by the time we left there was a line around the corner. We shared a delicious Florentine steak and the pastas were great. It’s the kind of place we could have stayed for ours drinking crafts of house wine. 

Cibreo Trattoria – we had a great lunch here on the way to the Jewish Synagogue. It’s also next to the Lisa Corti shop and the Mercato Sant Ambrogio – Florence’s gourmet food market which is fun to wander through and grab some snacks. 

Ditta Artigianale great artisanal coffee shop also close to our hotel. I think there are a few locations in Florence. 

Gelateria La Carraia a tiny little gelato place also close to our hotel, serving craft gelato using natural ingredients. Loved this place and they had a decent selection of nondairy options. 

Tuscany Recommendations:

Where we stayed:

Castiglion Del Bosco, a Rosewood property but really its own little town – a 5,000 acre medieval village that the Rosewood resort chain purchased and now runs. Castiglion Del Bosco translates to castle in the clouds and that’s truly what it felt like being there, it was by far the most special place we’ve ever stayed. Yes, it was very expensive but I’d say if you’re going to splurge this was the place to do it. You are paying for the service, the setting, the food, the experiences – everything from the rooms – each felt like its own little villa, to the cooking school on property, its own vineyard and vegetable garden to the little ice rink they set up and the most stunning indoor pool I’ve ever seen. I was worried there wouldn’t be much to do in Tuscany in December for the kids but it was actually the most perfect time to be there. They had tons of fun activities for the kids, even a kids club that you could drop into at any point during the day. The one excursion we took was a truffle hunt which was on my personal bucket list. 

What we did:

We really just enjoyed the property – it was super kid friendly so the girls could just walk over and pick up skates to go skating, we enjoyed the pool every day we were there – they build an entire glass structure over their outdoor infinity pool with a bar in the winter – it was probably one of my favorite parts of the resort. There was staff on hand brewing pots of fresh teas and always little biscuits and cookies available which the kids loved. There are several hiking trails throughout the property, pickleball and tennis courts which were open bike rentals for the more advanced riders as the property is very hilly. We did a brief wine tasting at the vineyard but mostly just enjoyed drinking the wine!  We signed up for a pasta making class with the kids which was also really fun. 

There are two restaurants which we ate all our meals at. Ristorante Campo Del Drago is resort’s Michelin starred finer dining restaurant. My husband and I ate here one evening, we opted for the vegetarian tasting menu it was delicious but didn’t feel the need to eat here more than once. 

The more informal Osteria La Conica is where we ate the rest of our dinners, they had a nice kids menu and options to order from the grill – I loved the grilled chicken and lamb and all the pizzas were delicious! 

Rome Recommendations:

Where we stayed:

Villa Agrippina Gran Melia – more of a resort than a typical city hotel we stayed here because they had family suites that could accommodate our family. It’s set slightly away from the center of the city, up the hill towards the Vatican. I actually think I would have preferred to be more the center of things, even though we were only a 10-15 min walk from most neighborhoods with the kids I think it would have been easier. The best part of the resort is probably the pool and outdoor cabanas which were closed in December. I heard there is also a kids club in the summer months – so probably consider this one if you’re visiting in warmer months. 

What we did:

I booked a few tours ahead of time which I’m glad we did. honestly Rome felt mobbed with tourists, all the sites had super long lines and we kept hearing it was nothing compared to the more popular summer months. I felt like we needed to see things like the Colosseum and the Vatican with the kids but honestly it was hard to enjoy with so many crowds, it felt a little like Disney being herded like cattle through the sites. I tried to limit the tours to 1.5 hrs max, if it included walking around a neighborhood than a little longer and always made sure to have tour guides include stops at special places for food which kept the kids energized and motivated!

Tour of old Jewish Ghetto – would highly recommend hiring a tour guide to walk through the old Jewish Ghetto, synagogue and museum. We found a guide, Yael through Jonathan at Tailored Tours Barcelona who we used last year when we took the kids to Barcelona and thought she was fabulous. 

Golf Cart Tour of the city – do it! Very efficient way to get around the city and check off all the important sites in a short amount of time. They even had a carseat for our three year old and he loved it! We combined it with a tour of the inside of the Colosseum and probably would have skipped that. I booked through our hotel but there are a bunch of different companies around the city. 

Vatican tour – I felt like we couldn’t leave Rome without seeing it, definitely get a private guide and try to go first thing in the morning or later in the afternoon. I also heard it stays open in the evenings during the summer months and is less crowded at that time. 

The streets in Rome were packed and the narrow cobblestone streets were a little difficult to maneuver with the stroller but I did enjoy popping into the vintage stores and more unique boutiques around Campo De Fiori. 

Food recs:

One of my most memorable food experiences was visiting a bakery in the old Jewish ghetto called Il Boccione and the address is Via Portico d’Ottavia, 1. Make sure to try the pizza Ebraica, a burnt biscuit with raisins, almonds and candied fruits. It is weirdly addictive.

The Trastevere neighborhood was recommended to us by several people as the place to go for dinner and drinks – we did end up there one night – it was definitely crowded and energized, it felt a little touristy, felt like the place all the Americans studying abroad would go to hang out but we had good pizza at L’elementare which was really good and definitely kid friendly – definitely tons of good bars around there but not necessarily places I would rush back with the kids for. 

Roscioli is kind of an institution in Rome – to get a table to sit you’ll need reservations well in advance. I had booked a table at the salumaria that I ended up canceling because we had just decided to pick up pizza from their takeaway the day before. I would definitely recommend at least making a stop in the takeaway bakery for that, even if you have to wait in line for bit it was worth it! Pizza alla pala is one of Rome’s oldest food traditions – its a thing pizza cooked on an elongated wood board and then you purchase it in smaller sections – its all over the city but was especially delicious at Riscioli  

Enoteca il Piccolo dal 1980 – Stopped here for wine and snacks, great wine selection, cute old place fun people watching.

If you’re touring the Vatican and need a quick lunch or coffee break check out Cafe Meme – we had delicious smoothies, salads and coffee, it’s super cute and perfect when you start to get sick of Italian food at every meal. 

Romanè – which was located outside the center of the city near the Vatican was definitely our favorite meal in Rome. It’s a newer restaurant and a more modern take on some Roman classics but everything we had was absolutely delicious and unpretentious.

Tips that made traveling with kids a little easier:

I always travel with packing cubes, especially when I’m with the kids and we’re packing and unpacking more than once during a trip. I use these ones from Amazon but there are a lot of different ones out there. To help with jetlag we take an overnight flight, the kids will usually sleep at least the majority of the trip (a little kids melatonin helps!) and then try to keep them up the next day until 8pm or just to get them adjusted to local time even if it means everyone takes a little nap in the afternoon that first day. 

This time around, I tried to arrange for a local babysitter in each city, I had the hotel concierge arrange and it actually worked out great. It allowed us to be a little more flexible with our plans, if one or two of the kids weren’t up for touring I was okay with them staying behind and going to a playground with the sitter – I tried to not overschedule either, building in more downtime during our days helped everyone. For our kids, breaking up the two cities with four days in the country was also a great decision. They loved having a little more independence and freedom at the resort and a little more space to roam around.  Overall I loved our itinerary and would definitely recommend the hotels in Florence and Casiglion Del Bosco with families. The weather was really perfect, I can’t imagine how much harder it would have been traveling in the heat of summer. We were able to bring lighter coats and the temperatures mid 50s-60s was perfect for pretty much walking everywhere. I’ve been to Italy many times before but experiencing it with the kids almost felt like seeing the country for the first time again. All in all I would definitely recommend!