3rd Time to Italy- But with 9 month old

Any recommendations as where to get our two airbnbs???

Here are two agriturismos you might like in Val D'orcia region of Tuscany:

https://www.bonello.eu/en/

https://www.agriturismoilmacchione.it/?lang=en

Any towns similar to Orvieto in terms of some nice flat areas, and many shops?

Lucca, Viareggio, and Pisa

Do we give Florence another try? It really did have great food and was cheap.

Yeah try Florence again or Lucca. Lucca is the best town in Tuscany for small children.

Are villages like Pienza "too small", we like the idea of relaxing, however we don't want to l too secluded either.

Pienza is fine

We LOVED Assisi as well but realized that its hilliness may not ideal for a babe at this age.
We already know to bring smaller stroller and baby carrier. etc.

Lucca will serve you better.

ohthebliss,
Sounds like fun! Congratulations on your upcoming trip. We took our then 7 month old to France, Switzerland, and Germany in 2017, so yes take the baby!

I don't usually stay in airbnbs or drive so sorry I can't help with that. We hotel and train.

Towns like Orvieto. How about Siena. The hill top doesn't seem as flat as Orvieto but, it is much smaller than Florence, has many shops, restaurants, and things to do. To me the character is a lot like Orvieto. The Duomo is beautiful with its striped black and white marble, and gold pediment. Rick has info on this website and videos if you're not familiar. If you're looking for a smaller village might I recommend San Gimignano. It's a small hilltop village with competing medieval towers. There's not that much to do but wonder around on old narrow cobblestone lanes however, that mat be ideal for the little one.

Florence is awesome, I love it. But if you're not interested, go where you like. I haven't been to Pienza.

I hope you guys have a great trip!

Another vote for Lucca. Within the walls there is very little traffic, its flat for pushing a stroller, and the park and walking trail on top of the walls would be ideal for taking a kid (keeping them close of course, the wall usually has no railings at the edge). Can day trip by train to many other sites easily.

My first thought for your wish list was Lucca, but I see it’s longer than a 3-hour car ride. Other nice, flat towns that I really enjoyed are Ravenna, Padova and Parma but also beyond your 3-hour ride.

I was in Pienza last summer as a day trip - a charming town, but I wouldn’t want to be there longer than two days. And Montepulciano and Arezzo are much too hilly per your request.

We also really like Siena. It’s not flat, but I think it would be fine with a stroller. The ambiance of the town is wonderful, especially in the evening.

One idea is to take the train (faster than driving) to Florence or one of the towns listed above and then rent your car for your leisurely day trips.

RJean: thanks for the Accommodation recommendations! Lucca Is a little further out but it looks like a great idea. It's tempting to go back to Orvieto because we love it but it would be nice to try something new!

K2wilde: Lucca is looking like a great option. I have heard it's not the best place to be with a car though so I'll look into paying for parking outside the city walls.

Jean: you make a great point about "training" in and then getting a car later! One of the perks of getting a car at the airport though is the cost of pick up and drop off at the same place. I did compare train travel from airport to ech of the places you mentioned and it's not much quicker than with a car. I have read and heard of those cities being great though! (We may still consider Lucca.) Is Sienna less hilly than Assisi? Sounds like its similar to Orvieto. Thanks for your point regarding Pienza. Sounds like its better to stay on a farm somewhere and hit up the smaller villages as day trips

“Jean: you make a great point about "training" in and then getting a car later! One of the perks of getting a car at the airport though is the cost of pick up and drop off at the same place. I did compare train travel from airport to ech of the places you mentioned and it's not much quicker than with a car. I have read and heard of those cities being great though! (We may still consider Lucca.) Is Sienna less hilly than Assisi? Sounds like its similar to Orvieto.”

The general consensus from participants in this forum is to not be driving a long distance (or sometimes even a short one) after flying overseas for your safety and the safety of others on the road. If it makes sense, take the train to some place like Florence, and then you can pick up your car when leaving Florence and drop it off when you catch the train back to Rome.

Siena’s terrain - I would suggest looking at “Siena Italy” photos on Google Image to get a good idea for you to compare. My memory is Orvieto was pretty flat, once we were up in the city.

Hi everyone. I'm headed to Italy 🇮🇹 and want to stay in Orvieto for a couple nights. I'll be traveling with my sister so prefer an apartment versus a hotel room. Any suggestions or recommendations in the old town area?
Grazie per tutti.