What is the prettiest town in Tuscany to visit?

If I had to choose only one, I would say Siena : its medieval center forms a coherent whole, and Piazza del Campo, with its shell shape, gives the town a character you won't find in Florence. The cathedral striped with black and white marble is also worth a visit. From Florence, allow about 75 km ; plan for a full day to wander and enter a few monuments, or a night if you want to enjoy the town after the day-trippers have left.

It's not necessarily the best choice if you're looking for a quiet little village: Siena is a real city, with sometimes steep streets and busy areas, especially in high season. On the days of the Palio, July 2 and August 16, the atmosphere is special, but the crowds and traffic restrictions can complicate your visit. For a smaller town on a more intimate scale, look instead at Pienza, in the Val d'Orcia; for palaces, museums and Renaissance art, Florence remains the most obvious choice. But for a first glimpse of medieval Tuscany, I would choose Siena.