Trip to Italy with a 2 year old; advice on potential itinerary?

Consider Umbria or the Piedmont for less crowds but with all the charming towns and vineyards.

Venice comes to mind. Or from Orvieto why not drive over to Montefiascone and enjoy the lake setting.

Need I state that a 2yr old will slow you down? Since you are going place you have been before do not expect the same pace as in the past.

Happy travels

My advice with young kids is to slow down. Especially since you said you want to just experience the culture, not necessarily check out every museum. I would base out if NO MORE than 3 places. 1 night here, 2 nights there, 3 nights next, etc, gets exhausting.

Pick a city for 4-5 days, then an agriturismo for 5-6 days, and the finish somewhere else for 4-5 days.

I would even consider just going a week each in 2 different places as well. Seriously, less packing and unpacking and repacking is better with kids.

We did a 3 week trip with our 2 year old years ago to Italy and Lugano. Definitely do not plan on spending only 1 or 2 nights at a location. The point of a vacation is to relax and enjoy. Lots of parks available for kids. And the Italians love children.

have a great trip!

Ok good idea so if we want to stay a few nights in Siena do you suggest driving straight there from Rome airport or is Orvieto worth a road trip stop? Might be a good place to let the kiddo run around a little? Although the 2 1/2 hour drive to Siena isn’t too bad just not sure how he will be after our long US flight

I can't imagine flying from U.S. with toddler, getting luggage, renting a car and driving to Siena. I wouldn't want to do that without a toddler.

I would take train to Orvieto and stay three nights. Rent car on last day if you think two days in Orvieto will be too long and you want to wander to other towns.

There are two year olds, then there are TWO YEAR OLDS. Which kind do you have? If you have a flexible, easygoing version this can be a really fun trip.

What time of year will you be going? I wouldn’t want to be in major stops in the crowded high season. Do you use a backpack or a stroller? I’m thinking about Siena and San Gimignano and other hilly cobblestoned places that would be hard with a stroller.

I think Suki has a great idea, especially since you’ve seen the sites before. Make it a different type of trip with more emphasis on a relaxed pace. I’d aim at one base with short side trips, but with the ability to just stay put and have fun. If your two year old likes the pool, an agriturismo might be just the ticket. In addition to checking out Umbria and the Piedmont, check Radda in Tuscany. There’s an agriturismo with a pool on within walking distance of town. Also from there you could make some great side trips.

So much depends on the kid.

I am a big fan of taking children on trips --- the point is not whether the kid remembers the trip or realizes how cool Rome is, but that we get to enjoy seeing them enjoy themselves in the moment in a new place. Plus sneak in some things we want to do, like churches or museums, too. And eat well.

Our two sons as toddlers were quite flexible and patient travelers who could skip naps, sleep anywhere, eat in restaurants, walk fairly long distances, and entertain themselves. No kudos to us, they were just like that. Our granddaughter (now 19 months old) is a lighter sleeper, but much like our boys were. Our grandson LOVED going to Italy with us (and his parents and little sister) when he was 3 almost 4, but he definitely found it more of a challenge. Couldn't sleep on the plane from New York, got cranky without a nap, woke up crying at night for most of the trip, didn't like walking, etc ---- anyway, you get the point. He would have been a mess if we'd changed locations every few days. Instead, despite a few rough patches, we all had a great time.

We stayed for one week in one place, a second week in a nearby place, then 3 nights in Rome. I highly recommend not packing up and moving any more than you really have to. Also, think about your son having jet lag the first few nights or even longer, and plan for that. Both of our grandchildren were awake at night a LOT for the first 3 or 4 nights, and we were all glad that we didn't have to move to a new location or have anything in particular scheduled during the day for a while.

I would vote for taking the train to Florence from the Rome airport (hey, or better yet, fly into Florence airport if you can!), and stay in an apartment within the medieval walls but away from the very center, for at least 5 nights. Train or drive to Siena and stay there for a goodly number of nights. Maybe just one more location. Take day trips. Don't commit to anything too much ahead of time (advance museum or train tickets, restaurant reservations, etc.) Take it slow.

Definitely the best way to enjoy Florence and Siena is staying in an apartment or a B&B downtown...there are a lot of them. It will give you the freedom to cook something quick grabbing some food to cook in the numerous small market you can find downtown, accommodating any need a 2years old has, and then go around visiting the city late in the evening without worrying about parking etc... The pace will be different this time, that's part of the wonderful 'game', having kids...In Florence I would suggest to visit Boboli garden and parco Delle cascine: history, nature and safety for the kid at the same time. You might choose to rent a bike with a baby-sit, there are several bike rental centers, downtown.
Pisa and its leaning tower and Lucca with the ancient walls (you can walk them) are wonderful options to do something different. I hope it helps!
https://www.apartmentsflorence.it/ Is an idea for apartment in Florence or Airbnb or booking are valid.

Thinking back to our trip with our 2 year old. Upon arrival to Rome, we planned on staying a night by the airport to start acclimating to the different time zone. Our daughter(turned 2 on the Switzerland part of our trip) didn't do well sleeping on the plane. But we had been to Europe with her before---just younger so I was expecting the worse. She woke us up at 2 AM and was ready to play. We got our rental car the next day and headed to Umbria where we were visiting family. She did great the rest of the trip.

Depending on what time you arrive in Rome you will probably be fine driving on to Orvieto as long as the driver got at least some sleep! We were just more cautious and had the time so didn't push it.

I think also that it depends on your child. Ours are very easy travelers; my now 6 years old enjoys a faster pace itinerary. You know your child, so plan accordingly. I don't like to drive as soon as I land. In your case, you could take the train to Orvieto and spend the night or 2.

You asked about other potential destinations: Lake Como is gorgeous (Varenna is good base, especially with a toddler, I did it twice); Venice is fun if you can baby wear.