Exploring Tuscany

Tuscany is best seen by automobile. I would tell you catch Civita di Bagnoregio and stay the night at Orvieto on the way north.

I assume you're staying in an agriturismo outside San Gimignano? We just rambled around from hilltop city to hilltop city during the days, including Certaldo, Volterra and Sienna. Florence is just about 45 minutes away, too.

Consult these websites. San Gimignano is fairly central, therefore towns in any of the 10 Tuscan provinces are within reach. The Grosseto province and the Massa/Carraraa province are a little farther, but still within 2 hour drive.

http://www.borghiditoscana.net/eng/index.html

Below are the less known hidden gems:

http://www.borghitalia.it/pg.base.php?id=5&lang=en

There are so many great towns you can visit on day trips from San Gimignano but a few that we enjoyed are Volterra, Siena, Montepulciano, Ovieto (in Umbria, not Tuscany) & Pienza. I liked Orvieto a lot and wish we'd spent more time there. I would suggest you leave Rome early in the morning and take a train to Orvieto (takes approx. 90 minutes). You can leave your luggage at the car rental agency there, explore the town all day and then make your way back to the rental agency in the late afternoon, pick up your car and proceed to San Gimignano. In Orvieto, I would suggest taking the hour-long underground tour; it's really fascinating. Volterra was also a great town that I would have liked to spend more time in. We loved the Etruscan Museum there as well as the alabaster shops, etc. Have a great trip.

Thank you all for your suggestions. We certainly appreciate them and will try to get to each place suggested.

What kinds of things do you enjoy doing? Wine? You can pick up a map of the black rooster trail and make your way through Chianti. Or go to Montalcino and visit the Enoteca di Piazza for some amazing Brunello tasting and views. Food? I think that there are a plethora of day cooking classes on this website. Art and history? Florence is a great day trip by bus from San Gimignano, but all of the little hill towns are full of history. Tuscany is the best place on earth to get lost and find a little roadside restaurant and stop for an espresso or glass of vino.

Enjoy!

If you enjoy wine, then Montalcino. They have many Enotecas in town, and I think almost 200 wineries in the immediate area that do tours and tasting. If you are interested in suggestions for wineries PM me. We only planned on two nights, then after 1 afternoon, decided to extend our stay by another night. We loved it, but then we are wine geeks. We also had great wine and food in the restaurants. The best mushroom lasagna ever! We stopped in Volterra and San Gimignano on the way there, and found Montalcino much less touristy.

San Gimignano is a nice little town with wonderful food shops and views!
I lived in Florence for about two months and my favorite places that I visited when I was in Tuscany were: Lucca (one of the best places to go and eat - the restaurants are fabulous!! and nice shopping; walking on the wall surrounding the city was so fun); Siena (the architecture of the cathedral, seeing the main piazza where the Palio is normally held, paneforte-lovers dream); Orvieto (also some nice food shops and wonderful cathedral; I also took the underground tour and enjoyed learning some of the history).
Further afield, the Cinque Terre is a must visit place. This small villages perched along the cliffs and the hikes between towns are spectacular and unique. Enjoy some pesto there! My favorite village was Vernazza but Monterosso is the biggest town with the most space, eateries and places to stay.

We really enjoyed Montepulciano and just happened to hit it on Sunday, which was their market day. Also liked Cortona and completely agree thatif you like wine, Montalcino is where to go. We went to three wineries there.