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The 5 Prettiest Small Towns in Tuscany

Italy Tuscany

October 12, 2018 by Andrea Szyper

There are so many things to see and do in Tuscany, it is easy to overlook some real gems. That’s why we recommend staying for a week or longer and renting an apartment and car in the countryside, like we offer on our Tuscany Untour.

Florence, Pisa, and Siena will be on most itineraries. But here is a handful of our favorite less-visited towns in Tuscany, places where you can stroll among the locals, sample regional specialties in intimate restaurants, restore your spirits in beautiful old churches, and drink in the beauty of the old town walls and the rolling hills beyond.

Here are our favorite small towns in Tuscany, along with tips to help you enjoy them.



Rebuilt as a papal city by native son Pope Pius II, Pienza is a perfect Renaissance town, its 15th century plan, layout, and architecture serving as a model for cities all over Italy. It was built as a papal retreat town and retains a lovely sense of balance and beauty in its flower-filled residential lanes and piazzas. The town’s Duomo includes beautiful paintings by the Sienese School. Other notable buildings include the Palazzo Comunale and the Palazzo Vescovile, which holds a splendid collection of paintings and sacred artifacts.

Tip: Pienza and the surrounding hillside is a hotbed of Pecorino cheese making. Sample various locally made young cheeses flavored with mushrooms, ash, pepper, and herbs.

San Gimignano

San Gimignano

The skyline of this perfectly preserved medieval hill town is unforgettable, with just over a dozen stone towers soaring above a town center that holds beautiful gothic and romanesque buildings. You’ll quickly see why the town is a UNESCO World Heritage Site. Climb up into one of its towers for a unique view. Towers like these were common in the Renaissance, but most fell in waves of war and rebuilding. Be sure to also visit the town’s many beautiful churches and to drink in the atmosphere or its gorgeous piazzas and facades.

Tip: San Gimignano is the best known of the towns listed here. Visit in the evening, after the tour buses have left. Stay for dinner and enjoy a glass of the local Vernaccia wine while watching the sun set behind the towers.


Recently named one of the most beautiful small towns in Italy, Buonconvento sits in the fertile plains of farmland just south of Siena. Take in the local life and good restaurants of this friendly medieval town. The Museum of Sacred Art is a standout, its gorgeous galleries well worth a visit. Stroll its quaint, cobbled main street and stop into the church of San Pietro e Paolo. A short drive outside of town, you can visit Monte Oliveto Maggiore, a gorgeous Benedictine Monastery surrounded by the rugged, rocky landscape of the Crete.

Tip: Visit on Saturday for the town’s festive and lively Market Day, when Piazza Gramsci fills with vendors and the locals flock to shop for produce, meats, cheeses, fast fashion, and housewares.



Winding steeply up a hill with breathtaking views from all sides, Montepulciano is itself a place of great beauty. With Etruscan origins, the history of this renaissance hill town runs deep. It is well known for its Vino Nobile, a fine wine you can sample at cantinas within the city walls or on vineyards beyond them. The town is full of gorgeous churches to visit, including its Duomo, Santa Maria delle Grazie, and the baroque Santa Lucia church. Its civic museum holds a nice collection of artifacts, regional paintings, and some Della Robbia terra cotta.

Tip: On the outskirts of town, visit San Biagio, a beautifully-domed 15th century renaissance church. You can admire it from afar or drive the cypress-lined lane up to visit it.



This beautiful hilltop town, perfectly sighted in the gorgeous Val d’Orcia, overlooks some of Tuscany’s most beautiful and lucrative farmland. The territory is zoned for Brunello, one of the country’s most important wine exports. Sample the wine in the town’s many cafes and excellent restaurants and drink in the medieval history of this walled town. First settled in Etruscan times, Montalcino’s history runs deep. Visit the town’s Duomo, stop into the fortress for a regal wine tasting, and walk the town’s ancient walls.

Tip: Visit in late October to enjoy the Thrush Festival, a harvest festival that includes medieval games and pageantry and brings the locals out in costume to strut and socialize.  

The Tuscany Untour is based in Montalcino and on farms and vineyards in the surrounding hills, with easy access to all of these towns and more. It’s a great option for a deeper exploration of the region.

Enjoy your time in Tuscany!