Tuscan towns better to see by car

If you'd like to boot around the vineyards & wineries, I'd highly recommend doing at least one of these three routes: - The Chianti wine route: Strada del Vino Chianti - The loop between Montalcino and Montepulciano: Strada del Vino di Montepulciano - The area around San Gimignano:
Strada del Vino Vernaccia di San Gimignano Google these to decide for yourself. Along any of these routes, there are lots of opportunities to see beautiful countryside and pretty villages, if you have a car. I have found that some of the farm producers along the country roads welcome visitors and you can also sample cheeses, etc..

joan, A few comments, especially if this is your first time driving in Italy..... One important point to note is that for driving in Italy, each driver must have the compulsory International Driver's Permit, which is used in conjunction with your home D.L. These are valid for one year, and easily obtained at any AAA office (two Passport-sized photos required, which in some case is offered at the issuing office). Failure to produce an IDP if requested can result in fines on the spot! Have a look at This Website for more detailed information. You may also want to search other Posts here regarding the Zona Traffico Limitato areas that are becoming increasingly prevalent in many towns in Italy. EACH PASS through one of the automated Cameras will result in a €100+ ticket! A GPS along with a good Map would also be a good idea. Be sure to also give some thought to the question of CDW. If you accept the CDW offered by the rental firm, it will be expensive but will provide "peace of mind". Some "premium" credit cards provide rental vehicle insurance, however I've found this to be somewhat complicated so I just accept that offered by the rental firm. Check the Car Rental section in Europe Through The Back Door for further information. Happy travels!

Diane has a great suggestion, the road between Montepulciano and Montalcino. Pienza is a great lunch stop (La Trattoria d' Luna!) and also stop in San Quirico d'Orcia very cute! We like Monteriggioni outside of Siena and drove from there to Volterra, a "can't miss" town IMHO. You can loop to San Gimignano from Volterra on the same trip if you like.

Where are making your home base? Some towns, while hard to visit via train, are easy to reach via bus, especially from Siena.

Thank you to everyone who responded to my question. Ken, we are staying in Cortona as a home base. Thanks again for all your advice!