1. Florence is the heart and soul of Tuscany. Its Duomo and Baptistery are magnificent but crowded with tourists. Florence has the Uffizi, which now must be booked months in advance with many famous paintings and sculptures. There are also Medici palaces and gardens. Stroll the Ponte Vecchio and many narrow streets and passageways. Visit the market for fresh produce, meats, and cheeses.
2. San Gimignano, the City of Beautiful Towers, is a classic medieval walled hill town, famous for its 14 surviving medieval towers creating a beautiful skyline visible from the surrounding countryside. The oldest tower dates from 1298, its duomo from the 11th century. In the interior of the cathedral, see the fourteenth century frescos illustrating the life of Christ.
Try its white wine, Vernaccia.
3. Lucca has one of the best-preserved city-walls in Italy. Atop the walls are paths and gardens, allowing you to walk completely around Lucca's historic center. Lucca has several towers from where you can get fabulous views of the city.
4. Cortona is the Tuscan hill town made famous by Francis Mayes in her book Under the Tuscan Sun. Surrounded by Etruscan walls, the city was founded around 3000 years ago. Cortona is built upon the more ancient Etruscan civilization .
Google map of Cortona.
Photo from fotostock, see more.
5. Montepulciano is built on a narrow limestone ridge. Montepulciano wine is called Vino Nobile. The city has one of the most impressive main squares in Tuscany and has many beautiful Renaissance buildings. Nearby is Montalcino with a castle at the edge of the town that has wine tasting. Continuing on along the scenic route, Pienza is a small, beautiful Renaissance town.
Picture from Lovely Planet.