We just got back from my dream trip to Italy with my family and I wanted to make sure I got everything down before I forget! I’m going to cover our itinerary, things we packed, tips for traveling with kids (grade school aged) and anything else I think you need to know!

Rome

We started in Rome but only had one full day which I would probably advise against. I do think that just one more day would have been fine though. There is SO much to see, but it was SO crowded (even in September). We arrived around 1:00 pm and took the train to our airbnb. Our host was amazing! I picked the place because of the high reviews and mention that they met you at the train and walked you to the place. I knew this would be helpful. Once there he gave us a bus pass, and wrote directions for how to get to our planned activities. I looked into hotels and airbnbs for our trip but airbnbs ended up being more in our budget, plus they have seperate bedrooms/beds and had much better reviews than hotels in the area. This specific one wasn’t walkable to the main sites but it was near the bus/metro/and train. Being out of downtown meant it was much quieter.

Our first afternoon in Rome I scheduled a “golf cart tour“. I knew we needed to stay moving to stay awake and that we weren’t going to have time to see everything so this was a great option. Our guide was just fine, but we were able to see more things this way.

Colosseum Kids Tour

The next morning we had a kid centered tour of The Coliseum and it was phenomenal! Our guide was amazing and kept the kids engaged so well. This was one of the best things we did on our trip. Even my 12 year old boy who wasn’t excited about the trip was into it.

After the coliseum we found a great pizza place for lunch (and to cool down). From there we walked through the Forum. This was just ok (it was so hot).

Next we had booked “skip the line” tickets for the Vatican. We had to take a very long and hot bus ride to get there. Honestly, we should have skipped it. We didn’t realize that the Vatican museums were basically one long walk and you can’t exit or skip rooms. It was so hot in there and crowded and just not pleasant. By the time we got to the Sistine Chapel we were so over it. If we had another day in Rome we could have planned that part better.

I did not do a great job picking dinner restaurants for Rome. I was trying to make sure there were things that the kids would like so that limited us a little bit.

Tuscany

The next morning we checked out and hopped on a train to Florence. Our longer trips we booked in advance online. You can pick your seats and there’s room for luggage. The high speed train is so great! A couple things to note about the train system: you often can’t go through to the platforms until 45 minutes before your train and there is no where to sit before and after that point. If you arrive early you can pay for the lounge. The platform number for the train doesn’t pop up until the train arrives so you have to wait by the monitors and watch. We had a lot of luggage for the 4 of us so wanted to make sure to get a spot for the suitcases in the designated area.

In Florence we picked up a rental car and drove to Tuscany. The rental car system was a little iffy and there was definitely a scenario that they would have closed for the day (Saturday at 1:00 before we got a car). It was about a 2 hour drive to our airbnb in Anghiari. We stopped at a grocery store (check out part 2 for what you need to know about grocery stores in Italy) and picked up a few things for the next 5 days. We were meeting up with my friend Simone from Germany. She was an exchange student with my family when I was in high school and we have stayed close. I found a great air bnb that fit our two family’s well.

Trail Ride in Tuscany

This was one of the highlights of my trip. Chloe and I did a 2 hour trail ride somewhere in Tuscany (this was about an hour from our airbnb in Anghiari.) I found the place with “Get My Guide” and picked it because there were lots of reviews talking about how safe it was. Chloe and I are both comfortable on horses so this was a very relaxing and fun outing and way to see the countryside.

We had planned 5 days in Tuscany with the idea that we would do some sight seeing but also some relaxing as well. I think this was key to surviving 12 days away from home. We were an hour from Arezzo so one day drove to the train station and then took the train into Florence. Our only plan there was the Uffizi and Academia. We were all starting to get sick so made it a shorter day and were back in time for dinner. I do wish we had more time in Florence. One highlight was lunch at a steakhouse. Florence is known for steak and it didn’t disappoint!

One of my favorite parts of this week was grocery shopping and cooking at the airbnb. We spent afternoons snacking on cheese and meat and bread by the pool.

Montalcino

After our stay in Anghiari we parted ways with my friend and drove to Montalcino. This part of the trip was all about wine tasting specifically for my husband. He had a recommendation from his uncle about a winery and we planned around that. I really liked the airbnb apart from the fact that it was at the bottom of the hill the town was on. So much uphill walking! This town was so cute and charming. Just the right size, we could walk it all in an afternoon. Not too crowded, and great food. We had to drive to the wineries but traffic wasn’t bad. I had to sit out the second day winery as our travel cold had gotten the best of me.

Venice

After Montalcino we needed to drop off our rental car in Florence (about a 2 hour drive). When we arrived to drop it off a bunch of streets were blocked off or the ZTL was turned on so we circled for about 30 minutes before I jumped out to go ask the office what we should do. The street the office was on was completely blocked (with zero communication to us about how to get to them). From there we had to walk baggage to the train station and then take the train to Venice. Once in Venice there are water buses and taxis to get further into town. We ended up taking the water bus. This air bnb is one of my favorites from the trip. Super close to the water bus station as well as restaurants.

I didn’t make many plans for this portion of the trip. I know everyone was going to be getting tired so I didn’t want to commit to many museums or activities. We took a gondola ride the next morning, but otherwise just wandered the city. I was pleasantly surprised with how good the food was there! I have been to Doge’s place and museums when I was in college and really liked it. We were hoping to take a boat to Murano or Burano Islands but everyone was so over traveling at that point.

Travel Delays

This is where things went sideways! My husband had been alerted to a train strike happening on our next travel day. We thought that was only going to affect the state trains so we bought tickets on a private train (italo) as a backup. After doing more research (thanks to chatgpt to be honest) I realized that some of the private trains were affected as well. We discovered that there were labeled “guaranteed” trains that we needed to find. Our original plan was to take a train around noon to Bologna. We ended up on a train around 3:00. BUT our other problem was that not all of the water buses and taxis were running in Venice! I wish I would have asked chat what potential issues the train strike could pose for getting out of Venice. Our airbnb was only 5 minutes from the water bus stop but we found out we needed to go across the city a bit to get to the only water bus stop that was running. (Luckily we only had two roller bags to deal with. These Walker Duffle bags saved us on that account.)

Bologna

Upon arriving in Bologna we then discovered that the taxis there were also super delayed! We waited in a line for over an hour before looking for a bus. It was another hour or so before getting on a bus, and getting to our air bnb. Long day! Our plan was to explore the city a bit but were out of time. (After booking plane tickets I found out there was a huge tile convention that jacked up hotel and airbnb prices so we ended up away from downtown a bit.) We were able to find an Uber to get us to dinner and scheduled an Uber for the next day. I had planned lots of extra time in case we had issues the next day too but luckily there were no problems. Overall I’m so glad these issues were only at the end of our trip.

I’m planning a separate post on things I wish I knew before traveling with kids to Italy as well as extra tips and tricks! Click here for that post!