Sant Gimignano: This town is famous for its tall medieval towers, ancient and rocky skyscrapers. Almost all the old town is for pedestrians only, so better leave your car at a parking spot outside the walls.
A true gem for eating out in Sant Gimignano is Dal Bertelli (Via Capassi 30). The menu has only two choices, but gourmet quality: Tuscan bread sandwich with finocchiona (a local and special salami, fragrant due to fennel seeds) or with pecorino cheese. Go early, as Silvano, the owner, will close when he runs out of bread 🙂
Also famous and delicious is Gelateria Dondoli, in Piazza Della Cisterna.
– Volterra: It became even more famous after being one of the “Twilight” filming locations. Etruscan archeological excavations and alabaster carving craftsmanship are the hits of this beautiful town. Don’t miss the golden hour, the colors here are truly amazing!
– Val D´Orcia: Valleys and hills, the very Tuscan landscape. It’s worth visiting places like Montalcino, Pienza, San Quirico D’ Orcia, Castiglion D’ Orcia, Bagno Vignone, Bagni San Filippo.
My favs are Pienza and Sant´Antimo abbey. Also Montepulciano, renaissance at its finest.
Try the simple trattorias, where the locals go. Also go gourmet shopping: truffles, pasta, spices, cheese, wine and salami… superb quality and less pricey than in Florence.