We have a seven day trip in mind for Chianti in Tuscany. We plan to center our stay in or around Radda.We are planning to visit the following cities during our seven days and would appreciate any recommendations you found in the way of restaurants, artisans, shops, activities, people, sites not listed in Frommers or other's travel books. Whatever gave you a better sense of Italy and the people. we are planning to see: Radda, Siena, Florence, San Gimignano, Montalcino, montepulciano, Arezzo, and Cortona.

My wife and I really like the little piazza in Greve. There are several shops around the triangular "square" and places to eat. Sit at the wide end of the piazza on a sunny day with a glass of wine and some prosciutto and melon and happily watch the world go by.

My wife and I always rent a car in Tuscany and go where the wind takes us. Yes, we book a hotel in one of the towns, but when we take off driving we never know where we may end up. We take the smallest roads, some dirt or gravel, that we can find. FOund some nice places for a picnic along the way also. We really like the area around San Casciano.
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Sorry, you are about 30 years late. Chianti has been diced and dissected from every angle. I do suggest the book TOP 10 TUSCANY by Reid Bramblett. That is as close as you will get.

send an email to [email protected] they provided me with a great itineary for the area that was off the beaten path. We actually rode the route by bicycle but you could do in car just as easy.

Hope this helps.

Top Ten Tuscany is a favorite of mine, too. For your original question about Chianti, drive 10 minutes from Greve to the teeny village of Montefioralle and eat lunch or dinner at la Castellana. Enjoy the views across the vineyards & hills.