Traveling to Tuscany in October

Interested in places to stay preferably in Chianti and Montalcino …thank you!

We’ve stayed in both Pienza and Montalcino and preferred Pienza. It could have been the options available and where we stayed. For Montalcino we stayed at the bottom of the village in a private apartment but didn’t love the hotel options in town.

We’re going in September and staying here. This property sits between Montalcino and Pienza right outside of San Quirico. I’ve gotten great feedback from 2 different friends who stayed there.

We were in Chianti 2 weeks ago for a day trip. Highly recommend a meal here. Wonderful food, service and family that runs it. Very well known in the regiond so reservation recomended

Excellent tasting at Tenuta di Carleone as well. 23 Classico another winner from them as well as the Guercio.

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Agree with Fred. Pienza is great, is centrally located, and very close to both Montalcino and Montepulciano.

Our favorite hotel in town, La Bandita Townhouse, also has a great restaurant

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Felsina is excellent for wine and olive oil tasting.

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My wife and I and 7mo old daughter at the time stayed at the Mastrojanni hotel just south of Montalcino in October 2022. We had a great time, just a short drive to Montalcino or other wineries. Small place I think only 10 hotel rooms, had great views. Breakfast at the restaurant there was really good, but I remember the dinner menu could have been a little bit better, not a ton of options.

Thank you all for the recommendations- very appreciated!

In Pienza I highly recommend eating here. https://podereilcasale.com/it/