Tuscany has its fair share of magical places. Bewitching landscapes, intriguing stories and fantastical legends are around every corner.  It’s a land of hidden gems, with hilltop towns that seem to sit atop clouds, mysterious grottos, ancient buildings and castles. Little wonder it has inspired so many artists, poets and saints throughout the centuries. Here we go in search of the fairytale places that are sure to put a spell on you.

7 Fairytale places in Tuscany

1. San Gimignano – Medieval Wonderland

San Gimignano is a Medieval marvel. A perfectly preserved town with ancient stone buildings and fourteen imposing tower houses. Enter its gates and every step seems to take you further back in time. There’s the stunning Piazza Cisterna and its picturesque stone well at its centre, Piazza Duomo and its myriad details. It’s a mixture of the romantic and the historic. And of course no trip here would be complete without a climb to the top of one of its towers. What a view!

Discover the top things to do in San Gimignano.

fairytale places in tuscany
San Gimignano – photo @Ben-Kerckx on pixabay

2. Tarot Garden – An artist’s fantasy land

Let your inner child run free in the Tarot Garden, a world made of exuberant colours and fantastical creatures. It’s not a theme park, but the work of artist Niki de Saint Phalle, where kids and adults can interact with the gigantic statues that inhabit the vast garden. Enter the imagination of a highly original artist and get lost in the details of her playful fantasy. You find it near the walled village of Capalbio, in the Maremma in southern Tuscany.

See more attractions in Tuscany that kids will love.

Tarot Garden

3. Devil’s Bridge – A bridge built by Lucifer himself

The ancient bridge over the river Serchio in Borgo a Mozzano near Lucca is a beautiful sight, with an eerie legend attached to it. The story goes that the builder working on the bridge couldn’t finish it in time, and asked the devil for help. The devil agreed but with one condition: that the first soul to cross the bridge would belong to him for eternity. The following morning, when the man saw his bridge had indeed been finished, he sent a pig trotting over it. The devil was scorned, and dived into the river Serchio never to be seen again. This bridge, known as Ponte della Maddalena or Devil’s Bridge, is one of the fairytale places in Tuscany well worth a visit.

=> Discover Tuscany’s top sights and attractions. And 20 amazing experiences you can enjoy during your trip.

4. Pitigliano – one of Tuscany’s “tufa towns”

There are dozens of scenic hilltop towns in Tuscany, and you can argue that plenty of them belong on this list, with picturesque narrow streets and flowery balconies and windows. But Pitigliano has something extra special. It emerges like an enormous higgledy-piggledy sandcastle from the tufa hill seeming to grow out of the very rock itself. The effect is such that you can’t quite tell where the hill ends and the houses begin. A magical sight indeed.

=> Find out about the tufa towns and the attractions of southern Tuscany.

tufa towns

5. San Galgano and the Sword in the Stone

In Tuscany we have our own legend of the sword in the stone. A tale that unfolds in a quiet and peaceful place known as San Galgano. Saint Galgano was a dissolute knight who, wanting to renouncing his life of violence and vice, thrust his mighty sword into the rock. He choose to serve God instead, retired on an isolated Tuscan hill and was eventually made a saint. A little round church, the Montesiepi Chapel, was built in his honour near Chiusdino and the sword is still here, for all to see. Nearby you find the enchanting ruins of San Galgano Abbey.

6. Fosdinovo Castle – A Tuscan ghost story

Perhaps more fit for a Gothic story than a children’s fairytale, the mighty Malaspina Castle of Fosdinovo in the Lunigiana region is an impressive sight. Imagine a foggy night, and the castle emerging out of the fog, the only light coming from a single window where a candle burns. It’s the setting for the story of Bianca Maria Aloisa, the ghost of this mansion. A young woman who was imprisoned here because she wouldn’t renounce to the love of her life. Legend has it the ghost of Maria Aloisa haunts the castle to this day. You can visit and also spend the night in the castle to meet the ghost in person.

If you like Medieval castles, you should check out the Top 8 Amazing Castles to visit in Tuscany.

unusual places to visit in tuscany
Fosdinovo Castle
Photo by Davide Papalini – Own work, CC BY-SA 3.0, Link

7. Boboli garden – The Buontalenti Grotto

The Grotta di Buontalenti can be found in the Boboli Gardens in Florence. The exterior and the internal rooms of the cave are extraordinary sights indeed. Covered with bizarre sculptures of stalagmites and stalactites, you’ll also see statues of Ceres and Apollo and signs of the zodiac. This large grotto was built in the 16th century, commissioned by Francesco I de’ Medici, who had a passion for alchemy. It’s a curious place that featured in Dan Brown’s novel “inferno” and Ron Howard’s “Inferno” film.

Enjoyed this post? You might also want to discover the amazing landscapes of Tuscany, and some charming small towns to visit.

=> 8 Good Reasons to visit the Uffizi Gallery in Florence!

fairytale places in tuscany
Bountalenti Grotto in Boboli gardens
Di I, Sailko, CC BY 2.5, Collegamento