Best small towns in Tuscany?

Ciao

Crete Senesi area is completly different, small towns: Asciano, San Giovanni d'Asso, Chiusure for a slow travel. Visit the Archabbey of Monte Oliveto Maggiore.

Abbazia di Monte Oliveto Maggiore

http://www.cretesenesi.com/site-transitoire-p-1_vis_3_172.html

regards

alessandro draghi

agriturismo Il Molinello

Hi, among small towns in Tuscany i suggest you to visit  Radda in Chianti, Gaiole in Chianti and Castellina in Chianti.

However i can also suggest you to visit the town of Arezzo. I let a photo of Chianti landscape near Gaiole and a site with a lot of indications for charming holidays in Tuscany http://www.weekendromanticotoscana.info/en

Rent a car, bring a GPS, and then get lost. It's amazing what you'll find by taking back roads and just exploring. :)  I echo the above towns. And, though "touristy," Siena and Lucca are still both worth a stop. Especially the latter. I loved it there.

San Gimignano is a stunning town with its towers and views, especially if you stay there for a night or two.  In the high season there are tourists during the day, but it is quiet and peaceful in the morning and evening.  If you can book a room with a terrace overlooking the countryside at the La Cisterna, the views are amazing.  The simply furnished hotel is in stone palazzo on the Piazza della Cisterna with its 13th century well. 

Montisi is authentic and wonderful (montisi.com) perched between Castelmuzio and Trequanda; and Bagno Vignoni for the hot mineral springs; but other nearby towns on "tourist" trail should not be missed:  Pienza, Montalcino, Montepulciano; Cortona; Arezzo. 

Well, actually there are lots of small towns to visit in Tuscany and they are all quite full of tourists... but I promise you there are not "traps for tourists", they are just so awesome tourists want to visit them! :-)

I recommend San Gimignano, Volterra, San Quirico d'Orcia, Pienza, Bagno Vignoni, Montepulciano, Loro Ciuffenna and the area of Chianti Aretino. 

I definitely love Bolgheri, so cute and full of nice places to tray the local wine.

All the Chianti Area is great... Gaiole in Chianti, Impruneta, San Casciano in Val di Pesa, etc...

If you have more time you should go and visit Pitigliano, Sorano and Sovana, the Tuff Cities.

Near the seaside, visit Pietrasanta and Colonnata where they make the great cold cut "lardo di colonnata"!