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What city to stay in Tuscany for friends who have never been

Hello,
Going to Italy Sept. 2025 and one friend wants to see Tuscany. Which city do you recommend staying in, Montepulciano, Montalcino or Pienza? Myself, have stayed in two of the three.

Thank you in advance,
Joan

Posted by
17 posts

Looking for same info. When you went did you like any places better than others and are you looking to be on a farm stay or more in city

Posted by
7084 posts

We love Pienza. Quiet at night, flat, easy to drive in/out of.

Second choice would be Montepulciano as long as mobility is not an issue- it is so steep it gets tiresome.

Posted by
46 posts

jgoldberg,
We stayed in an agritourismo near Pienza.Cannot remember the name currently. Sorry.
In Montepulciano we stayed near the city in an old Olive Mill but it was before 2010 (the olive Mill). Could walk into town.

Posted by
46 posts

Thank you for your reply's.
Do you have a recommendation for a hotel or agritourismo?

Posted by
15939 posts

All of those towns will require a car.
Montepulciano and Pienza are so close to each other that really doesn’t make a difference.

Posted by
2103 posts

We loved Castello di Spedaletto da Laura agriturismo near Pienza. We visited Montalcino, Montepulciano and Pienza as easy day trips. After 4 days we moved to the Chianti region near Grevein Chianti. Was great to see the different terrain and rolling vineyards.

Posted by
2103 posts

We just spent 2 nights at a b&b near Lamole. We ate both nights at Ristoro di Lamole, a small excellent restaurant overlooking many Chianti valleys. The food is exceptional but the staff are almost more so. The owner started the restaurant about 30 years ago. His 19 years son is eagerly becoming involved.