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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.

Arezzo

Arezzo’s main attractions are its magical main square and its churches, often linked to Piero della Francesca. But the best thing to do in Arezzo is simply to appreciate life in a Tuscan city that does not define itself by tourism. Beyond Arezzo, we recommend day trips along the arty Piero della Francesca trail to Sansepolcro and Monterchi. Our other favourite trips are to hilltop Cortona and to a chic wine estate.

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Camaiore

The Village of Camaiore is located in a valley surrounded by hills and the northern Appennins mountains. Camaiore has Roman origins as one of the largest encampments near to the city of Lucca and an important station along the Via Cassia. The origins of its name "Campus Maior" come from this.

In the Middle Ages, the town grew considerably thanks to the old Via Francigena. The city represented the Twenty–seventh stage during the journey of Sigerico Canterbury, and was called Campmaior by the Archbishop of Canterbury.

Now Camaiore is filled with many artistic treasures which include the Collegiate Church, Saint Peter's which is a Benedectine Abbey and in the village of Pieve of Camaiore there is a church which is an excellent example of a Romanic church and dates back to about 817 d.C.       

The territory of Camaiore is beautiful and known for its landscape and its small medieval villages like Monteggiori, Casoli, Gombitelli e Montebello. From their hillside positions there is a fantastic view over the sea and surrounding hills, while time seems to have stopped centuries ago.

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Castagnoli

Castagnoli lies in the southern Chianti and so, despite its sleepiness, is well-placed for cultural outings to Siena Gaiole in Chianti and Radda in ChiantiMontepulcianoSan Gimignano and Florence are further away but still make tempting day trips for culture-lovers. Closer to home, it’s all about dining in delightful inns and indulging in wine-tastings, often in castles or abbeys. Luckily, you can also explore the Chianti in a more energetic way, whether by Vespa, on an electric bike, or even on horseback.

This is just a taster to the Chianti. See our specific guides to top Chianti outposts, all accessed through our Destinations listings, For starters, check out our guides to GrevePanzanoCastellinaRadda and Castelnuovo Beradenga. Our additional Chianti guides cover Castagnoli, Volpaia, San GusmeSan Donato in Poggio and Vagliagli.

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Castellina in Chianti

Even if Castellina itself is a key attraction on the Chiantigiana, the Chianti Way also leads to forays to neighbouring Chianti wine hamlets, as well as to San GimignanoSiena and Florence. Castellina makes a great base for activities as varied as cycling and museum-visiting, wine-tasting and ice cream-slurping. Sample a cookery course or visit a sculpture park: Castellina has it covered.

This is just a taster to the Chianti. See our specific guides to top Chianti outposts, all accessed through our Destinations listings, For starters, check out our guides to GrevePanzanoCastellinaRadda and Castelnuovo Beradenga. Our additional Chianti guides cover Castagnoli, Volpaia, San GusmeSan Donato in Poggio and Vagliagli.

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Castelnuovo Berardenga

Castelnuovo Berardenga makes a mellow base for exploring Siena and the southern Chianti.  As well as driving to wine estates, you could visit others by bicycle. The Chiantigiana, the Chianti Way, is made for forays to charming Chianti hamlets and castles doubling as wine estates or centres of contemporary art. To wallow in a tempting thermal spa resort, visit neighbouring Rapolano Terme. Or get on an electric bike or Vespa and explore the countryside. As for cultural trips, consider outings to MontepulcianoSan GimignanoSiena and, though further afield, Florence, a two-hour drive.

This is just a taster to the Chianti. See our specific guides to top Chianti outposts, all accessed through our Destinations listings, For starters, check out our guides to GrevePanzanoCastellinaRadda and Castelnuovo Beradenga. Our additional Chianti guides cover Castagnoli, Volpaia, San GusmeSan Donato in Poggio and Vagliagli.

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Castelnuovo di Garfagnana

Castelnuovo di Garfagnana is a bustling town with road and rail links to Lucca, Pisa, Florence and the Versilia coast by Viareggio. The national parks of the Apuan Alps and Appenines are an easy drive away and open up a whole host of walks, nature and sports for your enjoyment.

The history of Castelnuovo can be traced back to as early as 740AD but within a century, the village had become an important town with defensive walls and castles. Its location enabled it to establish itself as a transit point for traders and visitors travelling to the northern areas of Italy. Over the centuries, the defensive walls and castles were enlarged and improved. In 1924, Castelnuovo became part of the Province of Lucca.

Even today, the defensive walls of Castelnuovo di Garfagnana play an important role in everyday life in Castelnuovo di Garfagnana. The walls contain the oldest parts of the town along with winding roads and small artisan shops. The more modern offices, residences, bars, restaurants and train station are outside of the walls.

Many local residents commute to work in Lucca, Pisa or Florence whilst a growing number are able to make a comfortable living from tourism or from the sale of artisan gifts and paintings.

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Colle di Val d'Elsa

Colle di Val d'Elsa lies in the heart of Tuscany, close to SienaFlorence and Etruscan Volterra, making it a handy base for city-based day trips. Colle di Val d’Elsa can also be a stepping-stone to the countryside, especially to the Chianti, including gentle meandering through wine country around Castellinaand RaddaFor medieval townscapes and towers, visit celebrated San Gimignano or quieter Monteriggioni, a hilltop town encircled by walls, and a former outpost guarding the northern borders of Sienese territory. Other activities include walking or cycling to Poggibonsi or a foray to a Chianti wine estate best-known for its thought-provoking sculpture trail.

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Cortona

With few must-see sights, Cortona is about wandering at your own pace and lapping up the views and medieval mood. Much depends how far you want to climb as the crowds disappear once you head upwards along incredibly steep streets. More mellow pleasures include indulging in an ice-cream and a passeggiata around the main squares. Popular day trips can take you north to Arezzo or south to Lake Trasimeno.

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Florence

Balance visits to galleries with wanderings in search of the perfect trattoria or the perfect view. Do buy a Firenze Card online. It’s somewhat pricey but after four visits pays for itself and means you can skip the queues and enter the top museums and monuments without wasting your precious time in Florence. It lasts for 72 hours and allows free admission to EU citizens who are under 18 but accompanied by a city card-holder. Alternatively, a Grande Museo del Duomo ticket accesses all the monuments on Piazza del Duomo. The official online ticket-booking site for state museums is B-ticket, but there are many unofficial ones.

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Forte dei Marmi

Forte dei Marmi is all about the summer resort and being seen in the right places. If you want more than beach-life and gentle cycling, then head north, towards Massa. If feeling in need of adventure, explore Carrara and the marble quarries in the Apuan Alps. This is elemental Tuscany, a stark contrast to cosseted Forte dei Marmi. If in need of cultural stimulation, head away from the coast to the closest art cities. Foremost among these are Pisa to the south, or LuccaPistoia or Florence to the east. If you want a taste of country living, with villas and rural views, then do the Lucca villa tour we describe below.

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Gaiole in Chianti

Hilltop Gaiole makes a great stepping-stone to explorations of local inns, wine estates and ancient abbeys. From the fortified monastery of Badia di Coltibuono to Castello di Brolio. a former Florentine castle with its gaze firmly fixed on its ancient enemy, Siena. The area abounds in wine estates and gourmet inns but there are enough challenging cycle trails to keep you fit en route. As for culture, consider day trips to Siena, Florence or charming Castellina.

This is just a taster to the Chianti. See our specific guides to top Chianti outposts, all accessed through our Destinations listings, For starters, check out our guides to GrevePanzanoCastellinaRadda and Castelnuovo Beradenga. Our additional Chianti guides cover Castagnoli, Volpaia, San GusmeSan Donato in Poggio and Vagliagli.

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Greve in Chianti

Greve, the commercial centre of Florentine Chianti, is a place for browsing for wine and foodstuffs. While there is little of cultural interest in town, the surrounding countryside makes for delightful pottering. From Greve, enjoy gentle hikes, along with scenic drives to neighbouring castles and medieval wine estates. Greve also makes a great base for cultural day trips to Siena and Florence, along with Chianti-based wine-tasting and foodie forays in the vineyards.

This is just a taster to the Chianti. See our specific guides to top Chianti outposts, all accessed through our Destinations listings, For starters, check out our guides to GrevePanzanoCastellinaRadda and Castelnuovo Beradenga. Our additional Chianti guides cover Castagnoli, Volpaia, San GusmeSan Donato in Poggio and Vagliagli.

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Grosseto & Maremma

Naturally a visit to this city is a must. It began to develop during the Etruscan period with a more extensive road structure being developed during the Roman empire, which includes the Via Aurelia, still existing today. During the medieval period many of the main Roman and original Etruscan villages were abandoned and Grosseto was constructed. It was then fortified by the Medici dynasty and has much history to offer, such as the stunning Piazza Dante, the city's main square and home to many important buildings and the Palazzo Provinciale; a beautiful neo-Gothic building, constructed from travertine rock.

Be sure to wear some good walking shoes as the city is predominantly pedestrianised and there is so much to see, including some great shopping. Local artisans produce quality goods in leather and pottery, but look out for the lovely jewellery, the designs of which are inspired by the Etruscan period. You will also be able to buy some excellent local cheeses and pork products and of course many wonderful local wines.

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Lecchi in Chianti

Lecchi lies in the southern Chianti and so is well-placed for cultural outings to Siena Closer to home, it’s all about contemporary art in vineyards and outings to the lovely Chianti towns ofRaddaGaioleand Castellina in Chianti. It’s also about the Chianti dolce vita, with wine-tasting tours, fine dining and rustic inns, including in castles. That’s in addition to cycle rides, Vespa tours and summer swims in the local river. It’s an outdoorsy lifestyle.Florenceand San Gimignano are further away but still make tempting day trips for culture-lovers.

This is just a taster to the Chianti. See our specific guides to top Chianti towns and villages nearby, all accessed through our Destinations listings, For starters, check out our guides to CastellinaGaioleGrevePanzano Radda Castelnuovo Beradenga and our general Chianti guide. Our additional Chianti guides cover Castagnoli, Volpaia, San Gusmè, San Donato in Poggio and Vagliagli

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Livorno

Livorno is a city in Tuscany on the shores of the fascinating Ligurian Sea, an area of the western Mediterranean. Livorno was founded in 1017 and can look back on a long history, although it only became an important port and a centre of wealth and culture during the Renaissance. During this period, many Greeks settled in Livorno, followed by Jewish, Armenian and Dutch settlers - merchants trading in grain, textiles and other raw materials - who left traces of their influence on the region's cuisine, language and religion. Livorno retains its traditional charm today and attracts visitors from near and far with its historic buildings and peaceful location.

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Lucca

Lucca can be as lazy or as active as the mood takes you. Cycle along the city ramparts or climb to the top of the city’s only surviving tower-house. Visit churches, villas, wine estates or grand gardens before hitting the Puccini trail. If feeling lazier, then attend a concert of chamber music in town or browse the speciality shop, often hidden behind elegant, old-world shop fronts.

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Montalcino

Montalcino offers a neoclassical Cathedral, a Gothic loggia, a Romanesque church and myriad alleys - but in the end it’s the medieval mood, the fortress and wine that lodge in the memory.

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Montepulciano

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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Monteriggioni

Monteriggioni lies in the heart of Tuscany, convenient for a day trip to medieval Sienaor evenFlorence Monteriggioni can also be a stepping-stone to the countryside, especially to the Chianti, including gentle meandering through wine country around Castellina in Chianti and Radda in Chianti If enthused by Monteriggioni’s medieval towers, visit celebrated San Gimignano or Etruscan Volterrafor more medieval townscapes and towers. For shopping for the finest crystal, visit medieval Colle di Val d’Elsa. Other activities include walking or cycling to neighbouring Montagnola or exploring a stretch of the Via Francigena pilgrimage route.

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Orvieto

Orvieto is all about the mysterious mood, both above and below ground. Savour the slow pace of life, from medieval meanderings to wine-tasting in this Slow Food city. Orvieto also acts as a springboard to several gorgeous towns in Umbria and Lazio, all seen on day trips. Beyond the city, our Top Tip in Umbria is mystical Todi, one of the most beguiling towns in Central Italy. Our other favourite day trips are both in Lazio: Viterbo, `the Papal city,’ and Civita di Bagnoregio, Lazio’s ghost town.

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Panzano

Enjoy a meaty feast in Panzano, which is a restaurant hotspot, before embarking on wine trails in the Chianti hills nearby. Visit a Renaissance villa and gardens linked to Leonard da Vinci or fly over the Chianti in a hot-air balloon. More simply, enjoy a great circular hiking trail between Greve and Panzano, along with scenic drives to medieval castles and estates. Panzano, set more or less halfway betweenSiena and Florencemakes a great base for exploring both cities, as well as San Gimignano

This is just a taster to the Chianti. See our specific guides to top Chianti outposts, all accessed through our Destinations listings, For starters, check out our guides to GrevePanzanoCastellinaRadda and Castelnuovo Beradenga. Our additional Chianti guides cover Castagnoli, Volpaia, San GusmeSan Donato in Poggio and Vagliagli.

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Perugia

Perugia is both the capital of Umbria and the perfect gateway to exploring the region. From visiting art galleries and people-watching on medieval squares to munching chocolate “kisses,” Perugia offers great variety. The regional capital also makes a superb springboard to exploring several of Umbria’s loveliest cities. For day trips, our top picks are spiritual Assisi, Lake Trasimeno and Gubbio, a medieval city in miniature – with full highlights covered in our Top Ten guide.

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Pienza

Pienza is an exquisite Renaissance doll’s house, almost too perfect for its own good. Pienza’s popularity has been boosted by its Unesco recognition and by its attraction as a film set. More heretically, visitors flock to the town almost as much for its superb array of Pecorino cheeses as for its perfect Renaissance architecture. The future Pope Pius II was born here in 1405. He commissioned Bernardo Rossellino to rebuild the village of his birth as a model Renaissance city. The result is what locals call a città d’autore, a city inspired by one vision.  After strolling around Pienza’s city walls for splendid views of Monte Amiata and Val d’Orcia, few can resist retreating to a quaint inn for lunch. Expect Pecorino sheep’s milk cheeses to be on the menu. The scenery around Pienza is equally lovely, with the town framed by chestnuts and cypresses, olive groves, poppies and sunflower fields.

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Pisa

Unlike most Tuscan cities, Pisa's religious centre is not inside the walls nor in the old town but marooned on the northern edge of town. Coaches decant day-trippers on the Campo Dei Miracoli, the `Field of Miracles,’ with selfies in front of the Leaning Tower the chief priority. Spare a thought for the rest of Pisa, which is full of intriguing corners.

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Pistoia

Pretty Pistoia is often dubbed `Florence in miniature’ for its vivid cultural life, quiet confidence and its concentration of art and architecture. It is this living culture that sets Pistoia apart from other cities of a similar size. Even so, Pistoia is a much-underrated Tuscan city, despite the boost given by its year in the spotlight as Italy’s Capital of Culture in 2017. The town’s historic heart is delightful and contains one of the loveliest main squares in Tuscany. In un-touristy Pistoia expect to have the Romanesque churches and modern art museums to yourself, even if the popular inns are often overflowing. When dusk falls, the lamp-lit shadowy streets of Pistoia still have an authentic medieval atmosphere. Franciscan monks stride along in their brown habits and rope belts, and the stone slabs outside the shops are laid out with goods for sale, just as they were in the Middle Ages.

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Radda in Chianti

Radda makes a great base for activities as varied as visiting a Chianti cashmere goat farm or taking in a centre for contemporary art. As well as drinking up wine estates, you could visit a wine museum or try a wine appreciation class. Or perhaps cycle to a vineyard. Even if Radda itself is a key attraction on the Chiantigiana, the Chianti Way also leads to forays to neighbouring Chianti wine hamlets, such as atmospheric Volpaia. As for culture, consider day trips to San GimignanoSiena and Florence

This is just a taster to the Chianti. See our specific guides to top Chianti outposts, all accessed through our Destinations listings, For starters, check out our guides to GaioleGrevePanzanoCastellinaRadda and Castelnuovo Beradenga. Our additional Chianti guides cover Castagnoli VolpaiaSan GusmeSan Donato in Poggio and Vagliagli.

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San Donato in Poggio

San Donato in Poggio makes a charming base for activities as varied as visiting abbeys and villas or exploring vineyards on a Vespa tour. As well as discovering some of the Chianti’s loveliest wine estates, you could learn how to blend your own wine. Hiking through the vineyards is another temping option. Magical ballooning trips run from neighbouring Tavernelle Val di Pesa. As for culture, consider day trips to SanGimignanoFlorenceor even Siena

This is just a taster to the Chianti. See our specific guides to top Chianti outposts, all accessed through our Destinations listings, For starters, check out our guides to GrevePanzanoCastellinaRadda and Castelnuovo Beradenga. Our additional Chianti guides cover Castagnoli, Volpaia, San GusmeSan Donato in Poggio and Vagliagli.

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San Gimignano

The towers alone make a visit to this medieval time capsule worthwhile, but San Gimignano abounds in quirky sights. Make sure to stay after the crowds have gone. As for the museums, note that one combined ticket allows access to them all.

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San Gusme

San Gusmè lies in the southern Chianti and, as such, is well-placed for cultural outings to SienaCastelnuovo Berardenga and MontepulcianoSan Gimignano andFlorence are further away but still a tempting day trip for culture-lovers. Closer to home, it’s all about visiting major wine estates occupying lovely villas and castles and indulging in wine-tasting tours, fine dining and rustic inns, including in castles. Work off the calories by horse-riding or cycling along special trails. That’s not forgetting bathing in hot waters in the spa town of Rapolano Terme.

This is just a taster to the Chianti. See our specific guides to top Chianti outposts, all accessed through our Destinations listings, For starters, check out our guides to GrevePanzanoCastellinaRadda and Castelnuovo Beradenga. Our additional Chianti guides cover Castagnoli, Volpaia, San GusmeSan Donato in Poggio and Vagliagli.

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San Miniato

San Miniato is all about mood and minor sights, along with major eating. San Miniato also makes a great base. If suffering from cultural overload, head to a cosy inn, a day spa or go bird-watching in the moody marshlands, the Padule di Fucecchio. For city life and cultural enlightenment, head to Pisa, to the west, or Florence, to the east, along with LuccaSan Gimignanoand the Tuscan coast at Marina di Pisa – all are appealingly arty day trips.

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Siena

Siena offers a gorgeous chiaroscuro main square, town hall and cathedral. But, in the end, it’s the intimate, medieval mood that lingers, from the secret alleys to the cosy inns.

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The Chianti

The Chianti is a place for pottering and chance encounters. It is delightful, whether explored by car, by bicycle or on foot, or ideally a mixture of all three. The Chianti makes a great base, from cultural day trips to Siena and Florence to wine-tasting and foodie forays, along with cycling trips.

This is just a taster to the Chianti. See our specific guides to top Chianti outposts, all accessed through our Destinations listings, For starters, check out our guides to GaioleGrevePanzanoCastellinaRadda and Castelnuovo Beradenga. Our additional Chianti guides cover Castagnoli VolpaiaSan GusmeSan Donato in Poggio and Vagliagli.

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The Tuscan Coast

These are our Top Ten Things to Do, from basking on beaches to dolphin-watching, from cycling the seafront to visiting coastal nature reserves. Unlike many destinations, in Tuscany you can combine culture and the beach. Just don’t attempt to cover the entire coast on one trip. Choose your base carefully.

If you want to visit the classic cities of art from your seaside base, bear in mind that these are mostly more accessible from the northern coast, notably the Versilian Riviera. Typical day trips would be to PisaLuccaPistoia or Florence. Instead, if you’re based on the southern coast, in the Maremma, close to Grosseto, then Siena makes the most logical day trip, reachable in well under two hours.

The coast ranges from partying resorts to family-friendly beaches and deeply secluded bays. The northern coast, the Versilian Riviera, tends to be more manicured while the Maremma, the southern coast, is wilder and more romantic. In between stretch sweeping sandy bays, often backed by pine groves.

On the Versilian Riviera, to the north, the resorts range from posing Forte dei Marmi to boisterous Viareggio, a sun-and-sand resort popular with Italian families. Just south, closer to Pisa, are smaller, family-minded, highly affordable resorts along the Pisan Riviera (Riviera Pisana). Continuing south leads to the Etruscan Riviera (Riviera degli Etruschi). This, the Livorno coast, reveals a series of smaller resorts with sandy beaches and nearby ruins of Ancient Etruscan sites. Just south lies Grosseto province, bordered by the Maremma coast, the gateway to the wild Maremma region. Along this lovely stretch of coast, fun-loving Follonica, chic Punta Ala and Monte Argentario have all confirmed their Blue Flag beach status. Overall, Tuscany boasts 19 locations.

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Vagliagli

Vagliagli borders the southern Chianti and so is well-placed for cultural outings to Siena and Castellina in ChiantiFlorence and San Gimignano are further away but still make tempting day trips for culture-lovers. Closer to home, it’s all about visiting a sculpture park and indulging in vineyard and wine-tasting tours, fine dining and rustic inns, including in castles. That’s not forgetting cycle rides, Vespa tours and gourmet picnics in the rolling countryside. It’s an outdoorsy lifestyle.

This is just a taster to the Chianti. See our specific guides to top Chianti outposts, all accessed through our Destinations listings, For starters, check out our guides to GrevePanzanoCastellinaRadda and Castelnuovo Beradenga. Our additional Chianti guides cover Castagnoli, Volpaia, San GusmeSan Donato in Poggio and Vagliagli.

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Val d'Orcia

These are our Top Ten Things to Do, from gentle drives to soporific spas, from strolls in moody hamlets to medieval abbeys and the vintage Nature Train – all set in Unesco-listed countryside.

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Viareggio

Viareggio is both a typical and atypical Italian beach resort. It’s typical in that beaches are well-run, family-friendly but rather regimented. It’s less typical in that there’s life beyond the beach. Nor is it just about being a summer resort - or being seen in the right places. Viareggio makes a good springboard for exploring Versilia, from cycle rides along the coast to drives that reveal the elemental hinterland around Massa and Carrara. For a sense of adventure, explore Carrara and the marble quarries in the Apuan Alps. This is wilderness Tuscany, a stark contrast to the coastal strip. For a cultural foray, turn away from the coast toward the closest art cities. Foremost among these are Pisa to the south, or Lucca, Pistoia or Florence to the east.

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Volpaia

Tiny Volpaia makes a quiet and timeless base that is hard to leave, despite the limited range of obvious activities on tap. The hamlet lies just off the Chiantigiana, the Chianti Way wine route, so is well-placed for forays to neighbouring Chianti bastions, such asRadda and Castellina. If you are a culture-lover, also consider day trips to San GimignanoSiena and Florence, all within reach.

This is just a taster to the Chianti. See our specific guides to top Chianti outposts, all accessed through our Destinations listings, For starters, check out our guides to GrevePanzanoCastellinaRadda and Castelnuovo Beradenga. Our additional Chianti guides cover CastagnoliSan GusmeSan Donato in Poggio and Vagliagli.

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Volterra

Volterra makes for the archetypal Tuscan town – before tourism took over. Enjoy the relative tranquillity to explore the Etruscan, Roman and medieval heritage before shopping for locally-produced alabaster or dining in an Etruscan cellar.

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