Tuscany Villa for 2 couples best area?


New member
Hello New Friends,
We are 2 couples in our mid 60's - fit and capable of all physical activities (and we enjoy long walks and hikes). We are planning the following trip in October 2025:
Fly into Florence (3 nights in an Arbnb without a car)
Rent a car and probably stay one night in Sienna
5 -7 days in Tuscany area in a villa. It's easy to find villas, but I have no clue as to the best area. I realize this is subjective.

So... what are our desires? By the sea would be lovely - but more importantly is proximity to the wineries. We will likely drive or rent bikes for wine tasting (maybe one day hire a driver so everyone can drink). We also want to be near restaurants (though we will likely eat in one or two nights). I read that Montepulciano is a good area - but even with that information, I am unsure as to where to start.

Villa needs are 2 bed, 2 bath (bedrooms must have king Americans or two twins - queen is too small) Not sure pool is necessary in October. AC is still desirable. Outside seating area for 5 pm wine. 300 a night per couple so 600 a night is fine. I've heard there are some wineries that actually have guest homes on the property. We want something quaint/with character rather than modern - though we'll be flexible. I think the area is what matters most based on our desires.

Thank you for any ideas! I appreciate your time.