I recently went to Rome and Tuscany with my husband, and 3 boys, ages 5, 3 and 5 months. Here is everything we did and how I rated doing everything with toddlers.
Day 1 and 2 Rome: Not Tuscany but we flew into Rome before driving to Tuscany.
Day one we walked around and just explored the area near our Air BnB. We were all exhausted and we were just trying to stay awake until a reasonable bed time.
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Day 2: We woke up early and took a taxi to the Vatican. We were at the Vatican by 8:30. This allowed us to skip long security lines. Other members of our party did the 2 hour Vatican tour, we skipped that knowing our boys would never make it. We walked through St.Peter’s Basilica and got to go through the Holy Doors. It was not something I would say I felt I needed to do before going, but now having done it I would suggest it. It was absolutely stunning. I do not feel like we missed anything by not doing the tour or seeing the Sistine Chapel. As we were leaving by 9:30-10 it was getting more crowded. My suggestion for going with kids is get there early. You are not allowed to bring strollers into St. Peters so you do not want to be in there with a large crowd. Also, make sure to have your shoulders covered ( I brought a scarf) Vatican 8/10 with toddlers if you go early
After the Vatican we bought tickets for the Hop on Hop off Bus. This is one thing I would absolutely NOT suggest doing. It would have been cheaper and easier to take taxis to each location we wanted to go. We never got off the bus after not seeing anything and the bus taking to long between stops. Also, it was hot and the AC was not working. Bus 1/10
All my son wanted to see was the Coliseum and I wanted to see the Trevi Fountain. During the day the Trevi Fountain is so crowded you would not want to bring your children into those crowds. We went at 7pm and immediately left, it felt unsafe and you couldn’t even get close to the fountain with the crowds. We decided before we left Rome the next morning we would wake up early to see both. BEST decision we ever made. We woke up at 7 am and went to the Trevi Fountain. At this time there were people there not but we were able to walk right down to the fountain and take our pictures and have the boys throw their coins in. We then got into a taxi and went to the Coliseum. The taxi dropped us off at the bottom of a small hill. We walked to the top and were able to get beautiful views of the Coliseum. Early morning Trevi Fountain and Coliseum 9/10 Day/ Night Trevi 0/10
Days 3-10 Tuscany
We rented a villa in Cortona. The Villa allowed us to have a pool to relax at and a place for the kids to run around outside. Each day we visited a different place. We rented vans that came with car seats and boosters. This allowed us to have the freedom to come and go as we would like. My husband drove and had no problems driving in Tuscany (Rome is a different story).
Towns visited:
Florence: We went by train. We did a gelato making class with Tulio Bondi. This was an amazing experience for the boys and incredibly interesting and delicious for the adults. We then walked through Florence just exploring the beauty. We found carousel in the middle of one of the piazzas for the kids to ride on. We shopped and we ate. We found a wine window to drink from. I absolutely recommend Florence with the kids 10/10 with babies, toddler and kids
wine window for mom and dad
Siena: Absolutely stunning. The Duomo in Siena was one of the most beautiful pieces of architecture I have ever seen. We did walk to the top of the tower and we were able to look out to the whole city. My 3 and 5 year old were able to climb the narrow staircase and make it to the top. We left the baby with a relative as it would have been too difficult to carry him up. I would not recommend taking anyone younger because the stairs are very narrow and winding and it is very high up. The views overlooking Siena at lunch were idyllic Tuscany. 8/10 Easy with older toddlers and kids.
Views from the top of Siena 
Montepulciano: We went wine tasting at La Ciarliana Winery. This was perfect for families. It was a small vineyard and we had a private tour of how the wine was made. We got to see the barrel room and then had our tasting. The kids did juice tasting, colored, and got prizes at the end. We then went to the town of Montepulciano. There was not much there to do. I would skip that. 9/10 for the vineyard 4/10 for the town with kids.
Montalcino: Here we did another wine tasting at Altesino Vineyards. This was a larger vineyard and there was space for the kids to run around outside. The wine was delicious and the host was so informative, however, there was not much for kids to do while we were wine tasting. I would say to skip this with young kids and find a more family friendly vineyard (there are plenty). Getting there were some of the windiest hill roads I have ever been on. Absolutely beautiful but would have been nervous to drive at night. 7/10 with kids. 9/10 without
Forte Dei Marmi: On this day we drove 2.5 hours to the beach town not many have heard of (thanks to Instagram I found it). It was AMAZING. Small beach clubs (Bagnos) line the coast. We went to Bagno Milano, a relaxed family friendly club. For the day we got a cabana for changing and storage and a tented area with lounge chairs. The kids played in the sand and in the water. They also had floats, paddle boards, and sports that the guest could use. You can relax on the beach while surrounded by mountains. The views are 10/10. On Wednesdays, Forte Dei Marmi has their famous market where you could buy anything imaginable. It was an amazing sight. When you head into town you will find their luxury stores and restaurants. They had playgrounds, train rides, and go carts for kids to ride. Unfortunately, we didn’t stay late enough to enjoy dinner here. Most restaurants did not open until 7 and a lot of stores closed for a break mid day. If traveling here I would recommend staying overnight to fully enjoy the town. 10/10 for everyone
Cortona: If you have ever seen Under the Tuscan Sun, Cortona is where it takes place. A beautiful town nestled on top of a steep hill. Pushing a double stroller up that hill was no joke. My bigger boys were able to walk it, making it easier on me. Cortona had great shopping and restaurants but not much for the kids to do. We went for dinner one night and lunch/gelato another. It’s beautiful to see but can be done in a short period of time. 5/10 for kids
If you are thinking of traveling to Tuscany with your toddlers, my advice pour yourself a Hugo Spritz and book the trip!
