Explore our essential guide to the best small towns in Tuscany. From the magnificent San Gimignano to famous Cortona, Monteriggioni and the undiscovered towns of the Maremma, this is the one stop list for any Tuscan trip.

No trip to Tuscany would be complete without a trip to to some of its picturesque hilltop towns. With quiet and idyllic squares, cobbled streets and ancient gates, these towns make fascinating places to visit and explore.

small towns in tuscany
San Gimignano – photo @Mariamichelle on pixabay

Explore scenic small towns in Tuscany

Apart from the main towns, the pleasure of visiting Tuscany lies in getting lost in the narrow streets of its many smaller towns. These are some of the sights that make Tuscany famous. Atmospheric hilltop towns where time has stood still for centuries.

If you’re after something quintessentially Medieval, head for one of the fortified hilltop towns such as San Gimignano. Perhaps the prettiest and most “Medieval” of them all. Nearby Monteriggioni will satisfy your thirst for history with its intact city walls crowning a small green hill. For sheer scenic value, both towns never fail to impress. Not far from San Gimignano, lovely Certaldo also deserves a visit.

Larger in size, Cortona and Volterra are amongst the most attractive Medieval small towns in Tuscany. You’ll find gorgeous views, and plenty of accommodation and restaurants on offer. Anghiari near Arezzo is another popular destination full of Medieval charm.

small towns in tuscany
Cortona – photo @vidalouca1970 on pixabay

Towns of the Chianti and Val d’Orcia

In these areas, famous for their scenic countryside, there literally hundreds of picturesque small towns. In the Chianti region choose from hilltop towns like Radda in Chianti, Castellina in Chianti and the lovely Montefioralle, perched on a hill above Greve in Chianti.

♥ Discover the most picturesque spots in Tuscany!

South of Siena in the Val d’Orcia you’ll find elegant Montepulciano and Pienza, the spa town of Bagno Vignoni, and Montalcino with its famous wines. Peaceful atmosphere and plenty of charm.

More trip ideas? Discover some fairy tale villages to visit in Tuscany!

top places to visit in tuscany in 2019
Pienza – photo @mbscuola on pixabay

Off the beaten track in northern Tuscany

Starting from the northern tip of Tuscany, Lunigiana is where you find Pontremoli and Bagnone tucked away in the mountains. In the Garfagnana area the most scenic towns are Barga, a lively place with a gorgeous Cathedral, and the walled town of Castiglione Garfagnana.

Best small towns of the Maremma

Suvereto and Campiglia Marittima are two lovely Medieval stone-built towns in Tuscany, both on the Etruscan Coast south of Livorno. These are good excursions if you’re spending your holiday on this part of the coast.

Further south in the Maremma region, Pitigliano is one of the most impressive sights in the whole of Tuscany. A town that seems to have grown from the tufa hill on which it is built. Nearby Sovana and Sorano, are the other two well-known “tufa towns” and well worth a visit.

maremma driving itinerary
Pitigliano – photo @lovefromtuscany

In the small towns of the Maremma time seems to have stopped. These are relaxing places with pretty stone squares and a slow rhytm of life. Among the most picturesque are Capalbio, Montemerano, Manciano.

As coastal towns go, they don’t get more sublime and scenic than Castiglione della Pescaia. Further south, Talamone is a small pretty fishing port that makes for a nice excursion.

Find more picturesque villages in Tuscany to visit. For more suggestions for your trip, check out our 20 favourite things to do in Tuscany.