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Towns and Villages in Tuscany

There are some truly spectacular towns and villages in Tuscany. From medieval hilltop villages, to larger towns with beautiful old town centres. Or if you prefer something a little more upbeat, there are several big cities packed with culture and entertainment. Each region in Tuscany has something unique to offer. Wander through the cobbled streets of quaint Italian towns and you will soon fall under the spell of Tuscany.

Some towns overlook rolling hills, endless fields with rows of vineyards and rustic castles can be spotted on the horizon. Sit and watch the world go by in a local Italian cafe, browse through quirky gift shops or admire the striking buildings that reside within the city walls.

Our private pool villas, hamlets and farmhouses are located within close proximity to Tuscany’s most impressive towns and cities.

Where to visit

We have all the information you need about all the regions and key places you should visit on your holiday to Tuscany, including the 3 main cities Florence, Siena and Pisa.

Northern Tuscany

The scenery throughout Tuscany varies quite considerably depending on where you go. The landscape and terrain in the North is very different from the South. Its unspoiled landscape is mountainous, more rugged and broken up with thick woodland.

Just like the South, it has traditional hilltop villages and medieval castles, but here the pace is much slower, despite the area being densely populated. As well as being by the breathtaking Apuan Alps, from most locations in Northern Tuscany you can easily reach the coast within a 30 minute drive.

Northern Tuscany offers the best of both worlds, soak up the sun on the beach, go hiking in the mountains, or visit amazing cities and towns such as Florence, Lucca, Pisa and Pistoia. Northern Tuscany may be less stereotypically Tuscan but it has classic architecture, artistic treasures, striking hilly landscapes and plenty of cultural events to enjoy.

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Central Tuscany

Can’t decide where to stay in Central Tuscany? Browse through some of the places below for further inspiration.

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Southern Tuscany

It’s easy to see why Southern Tuscany is such a popular area to visit, browse through the towns below to find out more.

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Umbria holidays

Umbria is often viewed as Tuscany’s sister, in many ways it mimics Tuscany’s delights, but also has its own distinct character. Umbria, known as ‘the green heart of Italy’ sits right in the middle of the country.

It’s about half the size of Tuscany, which means most of the region can easily be explored. Umbria is serene, understated, breathtakingly beautiful, and most importantly, unspoiled. It has long lived in the shadow of Tuscany, but visitors are discovering its charms and learning that a holiday in Umbria is not to be missed.

The landscape is littered with rolling hills, streams, valleys, olive groves and woodland. Visitors report there being a special quality of light that illuminates the horizon. Umbria is also famous for being the birthplace of the saints, which further contributes to its magical appeal.

This region is known for its olive oil, truffles, fine cured meat and full bodied wine. There are plenty of gorgeous hill towns to visit such as Assisi, Orvieto and Perugia, as well as quaint villages like Trevi, Spello and Montefalco. What are you waiting for? View the links below and book a holiday to Umbria.

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Val d'Orcia

The Val d’Orcia is a ravishing rural area running into le Crete Senesi, but within sight of hulking Monte Amiata. For many, this is the loveliest area in Tuscany, with Unesco-listed countryside, perfect hilltop villages, remote abbeys and evocative castles. Foodies, walkers and spa-lovers will take to the thermal spas, rustic inns, myriad wine trails and meditative walks. The Val d’Orcia represents quintessential Tuscany, with clusters of cypresses, ribbons of plane trees, vineyards on the slopes, and farms perched on limestone ridges. But it was not this alone that won the area Unesco World Heritage status – it’s also about the harmony between the Tuscans and their landscape, shaped by their mellow way of life. Once depopulated, these medieval villages are now enjoying a belated renaissance. San Quirico d’Orcia may be the gateway to the area but MontalcinoPienza and Montepulciano also make delightful stepping-stones to scenery landscaped since time immemorial.

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Experience an official tuscany tour with

Private Walking Tour: Florence and All Its Beauty

Explore the history and beauty of Florence with your private guide on a 2-hour walking tour. See some of the city's main attractions and personalize the tour to suit your interests, creating the most memorable trip to Florence.

from 162,1 US Dollar

Monte Senario Tuscany Bike Ride Including Florence Pickup and Lunch

Discover Monte Senario, a Tuscan abbey known locally as Santuario di Montesenario, and enjoy a leisurely bike tour through Tuscany before cycling downhill back to Florence. The full-day guided experience is suitable for all and starts with a minibus ride from Florence to Monte Senario. Pedal down toward the city through a nature reserve, and enjoy several stops on route to savor a 2-course trattoria lunch, visit a winery and take photos from the Etruscan town of Fiesole.

from 132,62 US Dollar

Bohemian Oltrarno Walking Tour with Olive Oil Tasting

Get out of the crowds and let's venture across the river in Florence. Start with a nice walk through the most exclusive "made in Italy" street of the city: Via Tornabuoni, cross the bridge and get into the city’s most characteristic artisan neighborhood: the Oltrarno, which literally means “beyond the Arno river.” Be ready to experience the real Dolce Vita visiting this pintoresque neighborhood where you will get to taste some traditional olive oil!

from 54,15 US Dollar

Lucca Round Trip Experience from Florence

Discover the city of Lucca and its treasures in comfort with this tour. A professional driver will guide you during an amazing daily round trip tour of Lucca. Visit San Paolino Street, Puccini’s birthplace (exterior only), the dazzling church of San Michele with its wedding-cake facade, the imposing Piazza Napoleone, and nearby Piazza del Giglio, the Romanesque cathedral housing the famous Volto Santo. The Volto Santo is a wooden crucifix supposedly made on the night when Jesus died.

from 383,5 US Dollar
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