The link below is exactly where I stayed. It was really cool and in an ancient town that has walking paths everywhere from village to village. It is in the heart of Tuscany, and great for day trips to Montalcino, Chianti, Montepulciano, Sienna, Florence (awesome), Pienza (home of Pecorino Cheese), and Cortona (where they filmed “Under the Tuscan Sun”). It is great villa and an awesome place to stage from. I even did a two day trip up to Pisa, and worked my way back along the coast. I started my trip with three days in Rome (no rental) and then went to the airport – rented a car and drove to the villa. I spent two weeks staged in the villa, and then eventually went back to Rome for a night before leaving Italy. It was probably one of the best trips I have ever been on (tied with France). There is so much too see and do; and lazy days in Villa are nice as-well. Italy was more expensive than I thought, (and the utility charge at the end of my villa stay was a surprise). I really like the villa approach, and if you can (if it is available) I would book the exact one I stayed at in the link below.

If you need anymore information, or want more detail – let me know

Villa
Late September/ early October is a great time to visit Tuscany. Less crowded and wonderful 70-degree weather. We've been 3 times; usually staying close to Montalcino. One of our favorite places to stay was in Serre de Rapolano (www.castellodelleserre.com), about midway between Chianti and Montalcino, where Salvatore and his son Antonio have refurbished a 13th century castle. They will not only feed you well, but also help you plan your winery visits.
We were there last year for the last week of September, first week of October. I highly recommend staying in or near Montalcino. There are several great places to eat in town and it is an easy trip to lots of places nearby. We had a blast exploring (get a relatively small car, the streets in towns are very narrow and tight)especially the "white" roads (meaning dirt and gravel lanes that wind through the countryside.

I would also caution against trying to go to Sienna on a Wednesday, that is market day and there is no way to find a place to park. So if you want to be there for market day, get there very early or take the train.

I'd also recommend making some appointments at wineries. I really enjoyed Costanti. There are plenty of places to go however, and that is harvest time so the vineyards might be heavy with grapes which is always fun. Unlike what Board-O said, everywhere was glad to have us there at harvest time and I even spent a couple of hours one day as a volunteer grape picker by just stopping at the vineyard and offering.

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