48 km south of Florence is the Medieval town Siena located, which its historical center is on the Unesco world heritage list. The city carries many historical treasures and traditions. For example a horse race, Palio, is organized twice a year (July 2nd and August 16th) , on the main piazza of Siena. This game attracts thousands of spectators every time. The most important and biggest building in Siena is the cathedral which began to be built 1229 but was interrupted several years due to the plague. Siena was in fact one of the cities in Tuscany worst hit by the plague and two thirds of the population died. Therefore, the cathedral was not completed until the end of the 1300s. To get to Siena, the best way is to take a bus from Florence central Santa Maria Novella.
If you are a twillight enthusiast you should not miss a visit to Montepulciano, a small town belonging to the province of Siena. On the main piazza scenes from New Moon where recorded. The easiest way to get here is to take a bus from Siena.
Between Florence and Siena Chanti is located, one of the most famous wine districts in Italy. The easiest way to get here is by car, but you can also book excursions with direct buses by different companies. Those often include Tuscan lunch, visits to vineyards and wine tasting.
The town of the towers, San Gimignano, belonging to the province of Siena, is located on the top of a hill with the beautiful Tuscan landscape around. This ancient town has its roots from the Middle Ages, and in 1990s it was added to UNESCO's host heritage list. San Gimignano has a main piazza, several beautiful buildings, churches and a large number of towers. To get here, the best way is to take a train to the main railway station of Siena and from there a bus to San Gimignano, but there are also companies that organize daily excursions with direct buses from various cities in Tuscany.
Pisa is one of the most popular cities in Tuscany, mostly due to its leaning tower on Piazza Dei Miracoli (where the cathedral of Pisa, the baptistery and the cemetery as well are located). It is important to remember that Pisa has several other beautiful monuments not to miss, for instance the church of Santa Maria della Spina, close to the Arno river or Piazza Dei Cavalieri. However, Pisa has one of the best shopping streets, so if you are in shopping mood Pisa could be a good destination.