Tuscany is famous for its charming small towns, Medieval hilltop hamlets and scenic walled towns rich with atmosphere. Here you’ll find some of our favourite towns that we recommend adding to your itineraries. We’ve chosen a few of the bigger hitters like Leonardo Da Vinci’s birthplace and enchanting Volterra, plus a few authentic gems you might not have heard of. There’s a town for every taste in Tuscany. Buon Viaggio!


CERTALDO ALTO – A Medieval jewel

The walled town of Certaldo Alto makes it a perfect day trip from Florence. It’s perched at the top of a hill 47 km. south of Florence and is easily reachable by car or public transport. Contained and charming, the main street via Boccaccio is everything you want a Tuscan street to be. With its crenellated palaces, flowered windows, the beautiful Medieval Palazzo dei Priori and cosy family-run restaurants, Certaldo can’t fail to impress even the most worldly visitor.

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VINCI – The home of Leonardo

Discover the birthplace of Leonardo da Vinci, a tranquil small town with beautiful views and a relaxed pace of life. It has a Leonardo Museum where you can learn about this multi talented artist and architect. Just outside Vinci, the house where Leonardo was born can also be visited. Nearby there are plenty of wine making farms for wine tasting and shopping. Vinci is 42 km. west of Florence.

PIETRASANTA – City of sculpture

Pietrasanta is a delightful small town in Tuscany situated at the foot of the Apuan Alps, 38 km. from Lucca. It has been shaped by its proximity to the marble rich mountains. The town is devoted to art, and you find contemporary sculptures all around the town. Small art galleries dot the streets and there’s an interesting museum dedicated to sculpture making. The charming Cathedral square is the perfect place to have a drink and soak up the atmosphere.

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charming small towns in tuscany

BARGA – Hidden passages and beautiful views

The main centre of the verdant Gargagnana valley, north of Lucca, surrounded on all sides by woods and mountains. Barga is a scenic small town that rewards the visitor with gorgeous views and a fascinating  Romanesque cathedral. One of the pleasures of a visit here is walking its steep and narrow streets and exploring the town’s hidden passages.

VOLTERRA – Meet the Etruscans

A day trip from Florence or Pisa, Volterra is one of those places that will conquer you immediately. With a distinctive Medieval feel, its narrow streets and handsome square, this town is a real delight. And if you’d like to know more about the Etruscans that inhabited this part of the world since 8th century BC, this is the place to come. The Guarnacci Museum is entirely dedicated to this ancient and mysterious civilisation. Local artisans still make jewellery inspired by their ancestors.

charming small towns in tuscany

LARI – Discover the castle

Lari Castle has been guarding its enviable spot above the Arno Valley (35 km. south of Pisa) since early Medieval time. Today this quiet and quaint small town is still dominated by the castle. With its massive walls and haunted prisons, it makes an interesting visit for kids an adults alike. You can enjoy beautiful, endless views from the castle over the valley, on good days you can see the sea. Off the main tourist trail, Lari is authentic Tuscany at its best. Nearby is the spa town of Casciana Terme.

RADDA IN CHIANTI- Views and wines

At the heart of the Sienese Chianti region, this hilltop town is justly famous for its stunning views and prestigious wines. The picturesque main square has a Medieval Priori Palace that speaks of its past, when Radda was the capital of the Chianti League. A day spent in and around Radda allows the traveller to unwind and enjoy the many pleasures of this beautiful area that has been devoted to wine production for centuries.


radda in chianti
Radda in Chianti

SAN QUIRICO D’ORCIA – Scenic landscapes and an ancient church

A tranquil small town set in one of the most scenic part of Tuscany, the Val d’Orcia (36 km. south of Siena). The drive to reach San Quirico is one of the most scenic ones in Tuscany, and its breathtaking views of the country are a good reason enough to venture here. But this delightfully peaceful place has an ace up its sleeve: the Romanesque Collegiata Church in local stone that seems to glitters with the sun. A real gem.

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SUVERETO – Get off the beaten track

Get off the main tourist trail and discover this small Medieval town a few kilometres from the Maremma coast. Suvereto has been listed as one of the most beautiful Italian borghi, and its narrow stone streets and impressive Palazzo Comunale will satisfy your taste for Medieval atmosphere. Check out the cloister of San Francesco and the small Romanesque church of San Giusto with a beautiful marble portal. Nearby Campiglia Marittima is also worth a stop.

SORANO – Timeless charm in the Maremma

Step back in time in this Medieval hilltop town in the heart of the Maremma. Expect steep cobbled streets, stone pathways, archways and the feeling of having left everything behind. This is a timeless place, with some magical views and buildings that have an air of faded beauty. A town to get lost in. Walk through its ancient gate and visit the fortress.

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charming small towns in tuscany