6 fairytale towns in Tuscany

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6 fairytale towns in Tuscany

10 May 2016

Tuscany is dotted with towns and villages that look like they’ve been plucked directly out of a fairytale. A walk behind their medieval walls and along their cobblestoned streets will inspire the storyteller in you.

Even better, these fairytale towns are located near several top wineries of Tuscany. Your idyllic walk in another land can end with a taste of the best Tuscan wines from Bolgheri, Maremma, or Brunello di Montalcino. You’ll never want to go back to reality.

Six fairytale towns to visit in Tuscany

Bolgheri

This tiny town that has given the famous wine its name is located just off of the Etruscan Coast. To reach it, drive through a famous road lined with towering cypress trees. Then, leave your car at the town's castle walls—no cars allowed inside this idyllic village! Once inside, wander the streets lined with trattorias, caffés, and wine shops with only the noises from the comfortable buzz of village life to keep you company. Bolgheri Bolgheri - © Ermess

Sassetta

Surrounded by chestnut forests, Sassetta looks like an isolated village in a children’s tale. It has hardly changed since it was first documented in the 11th century. The buildings and streets are constructed in stone, and some of its highlights include the quaint Woodland Museum (Museo del Bosco), Orlandi Castle, and a beautiful church and oratory. After exploring the charming niches of this town, head into the surrounding forest to the hiking trails that crisscross through the trees. Sassetta Sassetta - © Alessandra

Massa Marittima Massa Marittima - © Marnie Vaughan

Massa Marittima

Don’t miss this hidden jewel perched on a hill in Maremma. Massa Marittima has Etruscan origins, and traces of its ancient past can be seen throughout the town along the narrow streets that wind up, down, and around the town center. Its city walls and 13th century architecture remain perfectly preserved. The town is also known for being unique in its overall look, radiating a northern Italy atmosphere. You won’t see another one like it in the area.

Capalbio

Located in southern Maremma along the sea, Capalbio is a medieval town with red-roofed stone houses, picturesque piazzas (like Piazza Magenta), the stately Fortress of Aldobrandeschi, and a unique garden. Look out over Maremma territory from ancient, crenelated walls. Then, admire Renaissance-era frescoes in the 12-13th century Church of San Nicola. An artistic surprise awaits you a few miles from the center: the whimsical Tarot Garden, with colorful, larger-than-life sculptures by French artist Niki de Sante Phalle. They depict the twenty-two Major Arcanes of a tarot deck. And of course, don’t forget to taste a glass of the soft, fruity red wine made in the area, Morellino di Scansano. A little square in Capalbio A little square in Capalbio - © Yellow Cat

The Grand Wine Tour is a quality brand that certifies hospitality excellence in wineries that are part of its circuit. Explore and visit Altesino, Fattoria Le Pupille, Podere Sapaio

Montalcino

Take a step back in time. Montalcino, the town that gives its name to Brunello di Montalcino, is located in Val d’Orcia and has remained virtually unchanged since the 13th century. The ancient stone walls that encircle the town and its 14th century fortress are still in excellent condition. Climb to the top of its hill and look around. You will be surrounded by stunning views of the Tuscan countryside, gazing over vineyards, olive trees, fields, cypress trees, and small towns and villages. Town hall of Montalcino Town hall of Montalcino - © Sonja Pieper

Pienza

The original idea for this charming village in Val d’Orcia was to create the ideal Renaissance Town. In 1459, Pope Pius II began his project to transform his once unremarkable birthplace into a harmonic urban center. He hired Bernardo Rossellino to develop a city based on “humanist” ideals. The Pope died before its completion, but Pienza remains as beautiful today as he could have wished for, and is now a UNESCO World Heritage site. Il Chiostro, a former Franciscan convent in Pienza Il Chiostro, a former Franciscan convent in Pienza - © Any.colour.you.like

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