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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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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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Arezzo & Cortona

As you enter this region, you will quickly notice the hills of central Tuscany, which give the area a distinctly alpine feel. This part of Italy is home to the mountains that run through the centre of Tuscany.

Just on the other side of the mountains lies Casentino National Park in the province of Arezzo, it’s an area of outstanding natural beauty that’s ideal for all kinds of outdoor adventures such as cycling and hiking. Be sure to make your way up one of the peaks to watch the sunrise and take in stunning 360 degree views of the surrounding area.

In terms of city and towns, Arezzo is an inland city that’s not to be missed. It has a monthly antique market that attracts antique dealers from all around Italy, and is famous for its jewellery production. Although the city is flat, it is engulfed by the hills and mountains, which makes for a beautiful backdrop.

Cortona also lies within central Tuscany, it’s a really lovely town that’s known its impressive Duomo Cathedral and for being the setting of the book and film ‘Under the Tuscan Sun’.

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Lucca & Viareggio

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Pisa & Valdera

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Florence & Chianti

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Grosseto & Maremma

Situated in Southern Tuscany, this enchanting region remains completely unspoiled, it consists of 130 km of coast line with beaches, pinewoods and rocky shores are broken by numerous coves that are now tourist harbours: Punta Ala, Castiglione della Pescaia, Marina di Grosseto, Talamone, Porto Santo Stefano, Porto Ercole, Cala Galera and the harbours on the islands of Giglio and Giannutri. Known as the Maremma, it has a stunning and varied scenery which gives way to golden beaches and crystal-clear waters. The natural beauty also encompasses an incredible history and there are many archaeological sites dating back to the Romans. Add to the mix a wonderful cuisine and superb local wines, this part of Tuscany has everything you could wish for.

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Orvieto

Umbria, the birthplace of St Benedict and Francis of Assisi, seems bathed in a mystical glow, and Orvieto plays into the mystique. Set midway between Florence and Rome, Orvieto is Umbrian perfection, with luminous frescoes and enigmatic churches only serving to underline its lofty otherness. Looming on a sheer ledge of lava-stone, Orvieto is a brooding Etruscan presence hewn out of dark volcanic rock. In medieval times, this citadel, perched on its impregnable rock, controlled the road between Florence and Rome. Although majestically sited on top of a volcanic tufa plateau, the hill is porous and in danger of bringing the city down as it crumbles. More positively, the fertile volcanic slopes are covered in the vineyards that produce Orvieto’s famously crisp white wines. The town also scores high in the spirituality stakes, with its low-key churches counterpointed by the grandeur of the Duomo and loveliness of the undulating landscape.

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Perugia

The hazy hills, a magical quality of light, and an air of spirituality help set Umbria apart, along with its bewitching capital, Perugia. Cosmopolitan, arty, heritage-minded yet forward-looking, Perugia makes a delightful introduction to the region, with easy side trips to Assisi, Gubbio and Lake Trasimeno. Compared with Florence, Perugia feels far less tourism-led.

Umbria has often languished in Tuscan’s shadow but is just as lovely as its grander neighbour. Lap up the rolling landscape with hill-towns that look as if they have been there since time immemorial. It is not an illusion: some were founded by the Etruscans and later dedicated to medieval saints. Even if Perugia feels more secular than most of the region, Umbria is the cradle of western monasticism, with St Benedict born in Norcia. Beyond the tourism hotspot of Assisi, the region strikes a near-perfect balance between sustainable tourism and an authentic way of life.

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