Monte San Savino is a good choice for those interested in specifically Jewish history or just social history in general.
Lucca is a Renaissance town with well-preserved Renaissance walls and those cobbled streets that make you swoon.
Volterra is one of the most famous towns in Tuscany and one of the oldest.
It is best known for its ancient castle ruins and is another old town overflowing with history.
Looking for a historic old town with plenty of charm? Pienza is a charming town, and its historic town center is a designated UNESCO World Heritage Site.
Anghiari is another beautiful Tuscan town bursting with culture. However, Anghiari is famed for its artisan studios and antique shops instead of literature.
Certaldo is a beautiful medieval village in Tuscany. It is full of character and one of the prettiest Tuscan villages to visit.
The town has a unique layout, with buildings running in a narrow line down a steep hill, almost obscured by woodland.
Montepulciano is another one of Tuscany’s incredible hill towns. The quaint town is gorgeous with elegant palaces and dramatic architecture to admire.
Monteriggioni is one of the most beautiful towns in Tuscany and is located in its Chianti region.
Suvereto might be a bit too small to be considered a town, but it is so beautiful that it just had to have a place on our list.
It’s also worth mentioning that Cortona was the setting for the movie ‘Under the Tuscan Sun’ – so it is pretty enough to catch the attention of movie directors.
The town is enclosed in medieval walls that date back to the 13th century and is packed with medieval architecture.