Storybook villages in Tuscany are not in short supply. Small towns in enchanting locations, full of turreted towers, romantic archways, secret passageways and plenty of magical atmosphere. Go there and you feel you’re walking around inside real-life fairy tale. Just make sure to leave a trail of breadcrumbs behind you.

Once upon a time – Our top storybook villages in Tuscany

Capalbio – An enchanted walled village

Surrounded by perfectly preserved medieval walls, Capalbio will steal your heart with its ancient alleyways, hidden squares, old doors and picturesque corners. It’s a small stone paradise, with glorious views over the Tyrrhenian sea, flowers spilling from window boxes, secret passageways, and arches that lead you through an enchanted labyrinth of streets. A multicoloured creature guards the medieval gate. it’s a statue by artist Niki de Saint Phalle who also created the nearby Tarot Garden.

The Tarot Garden is a place where of wild and colourful imagination. The perfect way to round of a bewitching experience. It’s in Garavicchio, 6 kms. south of Capalbio, in the southernmost point of Tuscany.


2. Monteriggioni – Be a knight in shining armour

If there’s a place that conjures up the idea of Medieval legend more than any other, it’s Monteriggioni. Set on a natural hillock and protected by city walls, it has its own medieval festival every summer where you can enter into the spirit of the Tuscan middle ages.

In the small but fun “Armoury Museum” you can even dress up in full battle armour. Monteriggioni was a pawn in the battle between Florence and Siena for years, and has such a fabled past it was even mentioned by Dante in the “Divine Comedy”, where he compares its walls to “towering dreadful giants”.


Sorano – In search of the Etruscans

The hilltop town of Sorano, balancing precariously on a rocky outcrop, is a truly impressive sight. Seen from above, it looks as if a giant has fashioned the town from tufa rock itself. And once you step through the ancient stone gate of the fortress, you can forget the modern world altogether. Admire the majestic fortress and the medieval historic centre, and see how the rock seems to melt into the ancient buildings. This town, surely one of the most beautiful storybook villages in Tuscany, is surrounded by thick woods, from where you half expect some magical creature to come sauntering out.

More trip ideas? Check out our favourite small towns in Tuscany.

charming small towns in tuscany

Montefioralle – A timeless place among the Chianti vineyards

Montefioralle is a jewel created from stone. Once a castle, this tiny village sits on a hill above Greve in Chianti. You can still see the remains of the walls, a small church, and a few cobbled streets that follow the original medieval town plan. In summer it gets quite lively, but out of season it’s quiet and atmospheric, the perfect place to enjoy a tranquil stroll and gorgeous views over the surrounding countryside.

The Chianti region was a land of valiant knights and mighty castles, a place of legends that are still told today. The magic still resides in the cellars, where some of Tuscany’s finest wines are produced.

=> Discover how to choose a Chianti wine, and the top places to visit in the Chianti region.

Visit charming Siena, San Gimignano and Monteriggioni with this Guided Day Tour from Florence. Drive around the scenic Chianti countryside, visit Siena’s historic centre and then head to San Gimignano and Monteriggioni. Round off your day with a stop at a typical winery where you can taste some gorgeous food and wine.

fairy tale villages in tuscany

Bagnone – Magic in the “land of 100 castles” in Tuscany

At the northernmost tip of Tuscany, the mountainous Lunigiana region is home to some hidden gems. Bagnone is one of them, a grey stone village immersed in a landscape of ancient woods with a foamy stream of the same name running through it. Lunigiana was a strategic region in the Middle Ages, and today it’s known as the “land of 100 castles”. In Bagnone you’ll notice a cylindrical tower, all that’s left of the castle.

When you cross the stone bridge to enter the town, a magical world awaits, made up of narrow streets, flowered balconies and cobbled streets. The food here is straight out of a fairy-tale too.

fairy tale villages in tuscany
By Davide Papalini – Own work, CC BY-SA 3.0, Link

Porto Ercole – An ancient port, pirates and a runaway painter

In southern Tuscany there’s a spectacular mountain surrounded by the sea, called Mount Argentario. Porto Ercole is a small fishing port on one side of it, which has a long history and an ultra picturesque old town. This is the place where the fugitive artist Caravaggio came to die at a time when pirates were roaming the Mediterranean.

The historic old town, that you reach by climbing a steep set of steps from the colourful port, is a little gem. We visited in June, when bougainvillea was growing up the walls of the pastel coloured houses, next to creatively painted doors and sweeping views of the blue sea. You can follow the ‘Caravaggio itinerary’ though narrow stairs and picturesque tiny squares, to learn about the last days of the famous painter’s audacious life.

More trip ideas? Check out our favourite small towns in Tuscany, and if you’re in the mood for more magic, have a look at some of the region’s fairytale places.

Porto Ercole