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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.

Pistoia & Montecatini Terme

The area between Florence, Lucca and Pisa has always been highly sought-after – first by the warring factions who wanted to rule it, and, more recently, by those who love its prime location for a holiday. Montecatini Terme is one of Italy’s premier spa towns, known as much for its stunning Art Nouveau architecture as for the healing properties of its waters, which are thought to have drawn visitors since Etruscan times. Walled Pistoia, meanwhile, is perhaps Tuscany’s most underrated city, set around the yawning Piazza del Duomo, one of Italy’s most impressive squares, with a spectacular belltower clad at the top with zebra-striped marble. This is a great spot for families, with a zoo in Pistoia and the retro Pinocchio Park in nearby Collodi to visit. It’s also the heart of the area’s self-styled “chocolate valley”, renowned for sugary artisan treats, while the forested mountains rising up behind the two cities are good for hiking in summer and even skiing in winter.

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Montepulciano is effortlessly civilised and makes a beguiling base should you have a villa nearby. Its appeal lies in the mellow mix of Renaissance palaces and moody wine bars made for sipping Vino Nobile di Montepulciano. Like all quintessential Tuscan towns, it is built on a human scale so designed for strolling and relaxing on a Renaissance stage set, with set-pieces around every corner.

Architecturally, Montepulciano is “the Pearl of the Cinquecento” so shaped by the Renaissance. The town is Antonio da Sangallo’s masterpiece, just as Pienza belongs to Rossellino. While Pienza was perfectly planned, Montepulciano developed more freely so has an asymmetry and spiritedness that Pienza lacks. Even so, there is a loftiness about Montepulciano that makes itself felt in the noble palaces and equally noble wine. Even the citizens consider themselves superior, somehow above the fray. But ultimately Montepulciano is a smooth operator, delivering the true Tuscan lifestyle.

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Siena & Chianti

Wine fans should base themselves in the south of Chianti, a landscape that bucks the Tuscan trend with hills, often forested, that are more imposing than rolling, and topped by smaller chic villages. Holidays don’t get much more relaxing than pootling up, down and around these heavy hills, pulling over for a wine-tasting or a hearty Tuscan lunch. The area centres on three villages, Castellina in Chianti, Radda in Chianti and Gaiole in Chianti, but Panzano further north (technically in Florentine Chianti but spiritually southern) is making a foodie name for itself thanks to the butcher and restaurateur Dario Cecchini. Southern Chianti puts you within easy reach, too, of that Renaissance jewel, Siena. This city is famed for its shell-shaped Piazza del Campo, where tumultuous crowds cheer on the Palio horse race, but its treasures also include the Pinacoteca Nazionale gallery, which is filled with breathtaking art by the likes of Duccio and Simone Martini.

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The Tuscan Coast

In the annual `beach charts’ Tuscany triumphs. The region is recognised as having a superbly clean coastline, second only to Liguria’s. The beaches score highly for cleanliness of the water, safety, quietness, eco-friendliness and sustainability. Beaches are rated according to the trustworthy Blue Flags system. The sheer number of accredited beaches in Tuscany confirms the wisdom of opting for a beach break here. Not that it will ever be `just’ a beach break. What’s brilliant about the Tuscan coast is the proximity of beguiling art cities, hilltop towns and Etruscan sites. Yet given the length of the coastline and the competing claims presented by the cities of art in the hinterland, it’s best to decide on a couple of connecting coastal areas and to explore around there. Combine a villa-holiday near Viareggio with forays to Lucca and Pisa. Or, say, combine the beach at Castiglione della Pescaia with hiking in the Maremma.

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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

The beach town Viareggio and, further inland, chi-chi Lucca, couldn’t be more different at first glance. In fact, they’re an excellent pairing, not only to explore Italy’s architectural history but also live la dolce vita. Viareggio is one of Italy’s most elegant beach resorts, with grand Art Nouveau palaces and retro beach clubs along the perfectly raked sands. It’s also the location of one of Italy’s best-known carnivals (kids will love the Carnival Museum and the vast Cittadella, where the floats are made). Lucca, meanwhile, rolls back the centuries. Its oval main square takes the form of the Roman amphitheatre that once stood here, and the city walls are Europe’s second largest, fortified in the Renaissance. Scratch the surface and you’ll find Roman villas lurking beneath, including one mosaic-filled home below the church of Saints Giovanni and Reparata. This area was the stomping ground of the opera composer Giacomo Puccini – his birthplace is a museum in Lucca, and there’s a popular annual opera festival at Torre del Lago, just below Viareggio, where he later lived and was laid to rest.

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Pisa & Valdera

There’s more to Pisa than its Leaning Tower. Most visitors content themselves with a quick stop to see the dazzling Campo dei Miracoli, where that tipsily leaning tower is joined by a bone-white cathedral and extravagant domed baptistery. But the rest of the city, with its Gothic and Renaissance buildings, perched on the Arno river, is a peaceful joy to explore. Eastwards, towards Florence lies the Valdera, a Tuscany-in-miniature region of rolling hills crowned by terracotta villages and cypress avenues. History buzzes in unspoiled villages such as Palaia, and meets the present in modern art-filled Peccioli. There are quirky sights, too, such as the Vespas in the Piaggio Museum at Pontedera and the opera singer Andrea Bocelli’s open-air theatre for summer concerts, the Teatro del Silenzio, in the hills outside Lajatico. Volterra and San Gimignano are both easy to reach from here.

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Florence & Chianti

Few descriptions of Florence can do it justice. As the birthplace of the Renaissance, the city is arguably Europe’s art capital, its galleries full of works by the greats, such as Michelangelo, Donatello, Raphael and Botticelli, and its churches frescoed by the likes of Giotto and Fra Angelico. With Florence’s stately buildings and sprawling palace gardens lining the Arno river, this is one of Italy’s most strollable cities, despite the crowds. Surrounded by ruffled hills, the historic centre is just a few kilometres from the northern part of Chianti, which stretches from Florence and Siena to the south. This is a bushier, more rugged landscape than the better known Sienese part of Chianti further south; but it’s less visited, and therefore less spoiled, with vineyards and olive groves woven into wooded hills. The joy of this area is that you’ll be staying in a rural idyll with Florence on the doorstep, as well as other beautiful towns such as Impruneta and San Casciano in Val di Pesa.

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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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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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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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The Chianti

If the Tuscan lifestyle is the greatest lure, then Chianti is perfection. This famous wine-growing region is quintessential Tuscany, with villa-living the ideal way of appreciating the countryside. In the Chianti, the locals seem to have found the right balance between country and city living. The Chianti countryside is a patchwork of vineyards, olive groves and cypresses, or cornfields edged with sunflowers. Stretching from Florence to Siena, this soothing scenery, dotted with hill-towns, villas and castles, inspired the Renaissance masters. The art magnets of Florence and Siena are nearby yet feel far away. For those not fascinated by frescoed churches, the delights of Florence and Siena can often fade. The desire to escape the city’s cauldron-like atmosphere in summer can also prove overwhelming. If so, the Chianti is for you, with all its countrified temptations. Take it slowly, from meandering between wine estates to homely inns, castle-visiting and cycle trails.

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