See the Florence page for information about the capital of Tuscany.

See the Pisa and Lucca page for more about these cities in western Tuscany.

Learn more about Montalcino and its prized wine, Brunello, on the Montalcino page.


This old rival of Florence is one of the bigger cities in Tuscany, but still retains a medieval character in its mostly-pedestrian streets.  Its twice-yearly Palio (horse race) in the town square re-ignites that medieval spirit.  Also see Wikivoyage's Siena page for good tips.




The Chianti region, a large swath between Siena and Florence, is known for its wine, Chianti Classico.

Colle di Val d'Elsa

Colle di Val d'Elsa is a beautiful Chianti-region hill town known for its crystal.  The lower town is more workaday, and you can take a glass elevator to the upper, medieval town.

Other Chianti Towns

Countryside near San Quirico d'Orcia

Countryside near San Quirico d'Orcia - photo by Yosika

Val d'Orcia / Crete Senesi

The drive between Montepulciano and Montalcino, in an area called the Crete Senesi ("Sienese Crests") or Val d'Orcia, is some of the most pictoresque country in Italy—just about every stock photo and postcard of "Tuscany" is taken of hills and farmhouses along this drive, dotted with hay bales and cypress trees. Especially near San Quirico d'Orcia, this area is very photogenic. This article by Slow Travel contributors describes some of the most iconic photos (such as the Belvedere Farmhouse).


Known for its eponymous Vino Nobile di Montalcino wine, Montepulciano is a hill town at the eastern side of the Crete Senesi.  Recommended places to eat:


Perched between the wine cities of Montepulciano and Montalcino, Pienza is famous for both fresh and aged pecorino cheese (see this NY Times article for details).  Recommended eating places:

Other Hill Towns

For more ideas, check out Rick Steve's Hill Towns page.  

If you like hill towns, also be sure to check out nearby Umbria, which boasts such places as Orvieto, Asisi, Spello, Spoleto, and Trevi.


Famous for its alabaster, Volterra is Rick Steves' favorite Tuscan town.  Volterra has beautiful views and wonderful food, and more recently has gained fame due to the Twilight novels and movies (even though one of the Twilight movies was filmed in Montepulciano, not Volterra).

San Gimingiano

One of the only towns to still retain its medieval towers, San Gimingiano is popular with tourists but still a car-free, beautiful town.  It makes an easy day trip from Florence (by bus or by car); see this Rick Steves clip.


Tiny town about 40 minutes west of Florence with a beautiful view

Monte Amiata

...also check out Dissapore's 2017 list of best Trattorias in Tuscany (mostly in smaller towns)

Tuscan Coast

(Maremma/Grosseto province, Livorno Province, Massa/Carrara)

Arezzo Province



Featured in Francis Mayes' Under the Tuscan Sun, Cortona is another beautiful hill town, nestled on the Umbrian border.  Apart from the town itself, the Etruscan Museum is supposed to be quite good.  (Real Etruscan fans might want to go to the town of Chiusi, conveniently on A1 and train lines, which features an excellent Archaeological Museum as well as several Etruscan caves and tombs.)


Very close to the A1 highway, near the exit to Siena, Lucignano is a well-preserved medieval town with characteristic oval rings spreading out from its main piazza.