Tuscany Villa for 2 couples best area?

ellen495

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.
Cheers,
Ellen
 
Ciao Ellen, I somehow missed your post so wondering at what point of your planning are you and whether I can still provide some help - please let me know!!
October might be too cold for seaside the entire time, we never know because the last few years summer has extended and early October was still nice although not really hot.... and sometimes it got rainy in September! Overall, I would say the better base would be closer to wineries and if weather permits, do a day trip to the seaside!
 
I'd say look into the Chianti region. It's known for its wineries and charming villages. You can explore places like Greve in Chianti or Radda in Chianti; both have great wine and restaurants, plus they're close to other Tuscan gems. Montepulciano is lovely too, but Chianti might fit your needs a bit better.
 
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