7 Enchanting Storybook Towns in Tuscany That Feel Like Stepping Into a Movie

Pictured above: Sweeping valley views from Montepulciano

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When most people picture Tuscany, they imagine rolling hills, vineyards stretching toward the horizon, and medieval towns perched on hilltops.

And while cities like Florence and Siena deserve their fame, the real magic of Tuscany often lives in the smaller towns scattered throughout the countryside.

These places feel like they’ve been pulled straight from a movie set — quiet cobblestone streets, tiny cafés tucked into ancient buildings, and views that make you stop walking just to take it all in.

If you’re planning a trip to Tuscany, here are seven storybook towns that deserve a spot on your itinerary.

1. Bagno Vignoni

This tiny village in Val d’Orcia is unlike any other town in Tuscany. Instead of a traditional piazza, Bagno Vignoni has a large thermal water pool at its center, where steam rises in the morning light, creating a magical atmosphere.

Wander its stone streets, enjoy a café overlooking the warm waters, and take in views of the surrounding rolling hills. Stay in a gorgeous spa hotel that is just steps away from the thermal pool. Bagno Vignoni is perfect for those seeking authentic Tuscan charm off the usual tourist path.

2. Montepulciano

Montepulciano is one of Tuscany’s most dramatic hill towns.

Its steep streets wind past Renaissance palaces, wine cellars, and charming cafés. At the top of town sits Piazza Grande, a beautiful square surrounded by historic buildings.

Wine lovers will also appreciate all the options for trying new wines, and that this town produces Vino Nobile di Montepulciano, one of Tuscany’s most respected wines... and honestly, one of my favorites!

3. Buonconvento

Buonconvento is one of those Tuscan towns that feels wonderfully untouched by mass tourism.

Located south of Siena, this small walled village is officially listed among Italy’s most beautiful villages (“I Borghi più belli d’Italia”). Walking through its narrow streets, you’ll find terracotta buildings, quiet courtyards, and charming trattorias where locals gather for long lunches.

The historic center is surrounded by medieval walls, and the main street is lined with flower boxes, artisan shops, and cozy wine bars. It’s the kind of place where you can slow down, order a glass of local Brunello, and simply watch daily life unfold.

If you’re looking for a Tuscan town that feels authentic and relaxed, Buonconvento is a perfect stop, and stay in an agriturismo to indulge in comfort, relax by the pool, and experience what true Tuscany is all about.

4. Anghiari

Anghiari might be one of Tuscany’s best-kept secrets. This medieval town sits high on a hill near the border of Umbria and offers incredible panoramic views.

Its narrow streets twist through ancient buildings, and walking through town feels like stepping back several centuries.

If you plan to stay in Anghiari, there are some hotels available, agriturismos, and entire villas you can rent.

5. Cortona

You might recognize Cortona from the book and movie Under the Tuscan Sun. Anyone who loves Italy has likely seen the film (one of my favorites). And don't expect to find the giant, impressive fountain that was displayed in the movie. It was just a prop.

The town sits on a hillside overlooking the Val di Chiana valley. Inside the town walls, you’ll find cozy restaurants, artisan shops, and quiet piazzas perfect for people-watching.

Cortona can easily be your base if you want to stay there. Or you can do day trips from other Tuscan towns. Don't skip out on booking a pasta-making class in a local chef's own private kitchen!

6. Volterra

Volterra has a slightly mysterious atmosphere thanks to its Etruscan history and ancient stone walls.

The town feels less polished than some of Tuscany’s other destinations, but that raw authenticity makes it incredibly charming.

It’s also known for alabaster crafts, which have been produced here for centuries.

7. Montalcino

Wine lovers should not miss Montalcino.

This small hilltop town is home to Brunello di Montalcino, one of Italy’s most famous wines.

The town itself is quiet and beautiful, with medieval streets and a fortress offering sweeping views of the surrounding countryside.

Why Small Tuscan Towns Are So Special

While major cities draw the crowds, smaller towns offer something different. Life is slow and calm. Restaurants feel more personal.

And it’s easier to experience the simple pleasures that make Tuscany unforgettable — a glass of wine at sunset, a quiet walk through ancient streets, or a long lunch overlooking the hills. Sometimes the best places aren’t the ones everyone already knows.

With their winding streets, stone buildings, and sweeping countryside views, these storybook Tuscan towns feel like the kind of places where movie scenes come to life.