From time to time, people ask about places to visit in Tuscany that are a bit less on the tourist radar than, say, Montepulciano or Greve. We found two on our recent trip. The first was Pietrasanta, which we visited from our base in Marina di Massa. (I'll be putting up a review of our hotel there, shortly.) It's located near Carrara, so no surprise, there's a big emphasis on sculpture. Outdoor, modern sculpture abounds throughout the town The piazza del Duomo is attractive, and the streets leading off it have some nice shops and restaurants.
Our second find was Massa Marittima. It has a very pretty duomo and other attractive buildings in the medieval, lower section. The upper "new" section (14th century) also has some noteworthy buildings, like the clock tower. We were utterly charmed by the director of the Antique Organ Museum, who personally guided us through, demonstrating several of the instruments and showing us his repair works in progress. We stayed at the Hotel Duca del Mare, which we found to be clean and reasonably priced, with nice rooms. The people who run it are extremely friendly and helpful.
Montecatini Terme, a spa town in central Tuscany - we stayed for a week. Good sized town on the railway, so it was easy to do day trips from there to Lucca, Pisa, and La Spezia (to connect to CT). We stayed at the Grand Hotel Croce de Malta, which was very nice and was easy walking distance to "downtown," most of the spas, and the train station. There's also an older upper town (Alto), reached by an incline rail. My favorite restaurant in Alto was W.O.W. (Windows on the World), with views down over the valley. The main town has 8 or 9 spas and our small group trip included 3 spa entrances. My favorite one had a large indoor heated pool with water "cannons" and a cyclo-spa (kind of like lying in your own private hot tub while pedaling a bike - very relaxing!).
I have two - Pienza and Chianciano Terme. Stayed in CT for a whole week at Stefano's agriturismo and enjoyed it (minus the allergies to hay). I would return to both in a heart beat.