Some of us travel to Tuscany for a specific sight: Pisa’s tower, Florence’s duomo or Ponte Vecchio, Siena’s liquorice-striped cathedral or the whole of magical medieval San Gimignano. However there is so much more to this fantastic region, and that’s where our guide to Tuscany’s towns and centres might come in handy. We can help you decide where you really need to stay, or you can use our guide to help plan your grand tour, taking in all the sights.
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One of the most glorious cities on the planet, not just in Tuscany, Florence is rich with architecture, art, history, cuisine and scenery. It’s both very Tuscan, and entirely Florentine, a confident historic power which preserves its golden age, yet has a contemporary side too. It will take you a month or more to see all the sights, so don't be too ambitious — make a short list of the places you must see, eat well, and admire all the views. Florence is big enough to have a huge variety of accommodation, but surprisingly the larger hotel chains haven’t done so well here. Instead you'll find exquisitely converted palazzos, and heavenly villas in the hills, as well as hotels and B&Bs of all shapes, sizes and styles. There are plenty of aparthotels too, lots of family friendly options and properties galore for romantics and luxury lovers.
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Siena has one of Italy’s best known sky-lines, a marvel in shades of terracotta, ochre and siena, spiked by the black and white striped cathedral tower, and Siena’s many bell towers. There’s an argument to say that the best places to stay in Siena are the places with the best views; luckily, there’s a huge range of accommodation with fantastic views, in a range of price brackets too. If you want to stay in the centre of town, close to Piazza del Campo, the art galleries, museums, churches and cathedrals, towers, and historic-feeling shops, you’ll probably end up in a palazzo, villa or mansion conversion, or a townhouse turned B&B — Siena allows very limited building. If you prefer more contemporary accommodation you’ll find it outside of the city centre.
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There’s a lot more to Pisa than an architectural project gone slightly awry, but the tower certainly draws the crowds, who may otherwise have missed Pisa’s impressive number of museums and galleries, its beautiful spot on the River Arno, and walkable historic centre. Pisa is old, it was a maritime power before the Roman period, so it has plenty of tales to tell, but it’s also surprisingly youthful, kept young by its large population of university students. Pisa has some incredibly historic buildings, and an impressive calendar of events and festivals, but also a lively nightlife, and a very varied collection of accommodation and places to eat and drink. There’s plenty of great value to be found in Pisa too.
San Gimignano is a comparatively small town, but it’s entirely Heritage Listed, which means it has become something of a quintessential Tuscan hilltop town. Its narrow alleyways and open piazzas boast buildings in traditional Tuscan colours; there are bell towers, palazzos and churches a-plenty and a gelateria with a mind-boggling number of flavours. However because of its relatively small size, there’s not a huge range of accommodation available in town. But because most people come here for a day trip, there are big rewards for guests who do stay over, especially if it’s for more than a single evening. San Gimignano is quite serene once the crowds have departed, and there are some wonderful places to eat and drink which are impossible to find a table in during the day.
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Montepulciano, a familiar name to anyone who likes a glass of Tuscan wine, is a hilltop town (it is perched on one of the highest hills in the region) with loads of charm, some world class restaurants, and wonderful views over the surrounding region. The town boasts classic Tuscan colours, and an impressive array of architecture — look for the Renaissance highlights. As with all of Tuscany’s hilltop towns, there’s a limit to how many restaurants, and accommodation options, you can fit within the original walls, so Montepulciano is known for its restaurants with rooms. It also has some beautiful villa and farmhouse conversions, small hotels, and B&Bs. And if you’d prefer something a bit more contemporary you will find options just outside the ancient walls.
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Well positioned between some of Tuscany’s biggest hitters: Florence, Siena, Montepulciano, Perugia and Assisi, many people find Arezzo on their itinerary for practical purposes. But they’re very glad of it once they see Arezzo’s Renaissance palazzos and Romanesque churches — especially the Basilica San Francesco, with its incredible murals. People may also be glad of it once they see Arezzo’s shops and markets: Arezzo hosts one of Italy’s largest antique markets on the first weekend of every month. It is a bit less restricted than other Tuscan towns because it runs along the side of a hill, rather than sitting on top of it, which means the town has been able to develop with more freedom, and there’s more choice when it comes to accommodation here. Opt for a converted townhouse or Palazzo in the centre of town, or a converted abbey or Tuscan estate on the outskirts.
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San Vincenzo isn’t another of your idyllic hilltop towns, this is a Tuscan coastal town and beach resort, with golden sand and cobalt water on one side, and lush pine forests and olive groves on the other side. If you’d like the simplicity of a beach resort, you'll find that here, but if you’re more interested in San Vincenzo’s historic architectural treasures, then you’ll find plenty of accommodation to match: converted townhouses; magnificent villas, and repurposed farmhouses in the hills. San Vincenzo’s location, between Piombino and Livorno, makes it a useful base for exploring the Etruscan Coast, it’s also close to the Rimigliano Natural Reserve, and Elba. This is also a great pick for sailors
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Greve in Chianti is probably best known for its medieval market triangle (rather than square), lined with elegant low-rise shops and arcades and the fabulous church of Santa Croce, which has a superb art collection. Oh, and for having ‘Chianti’ in the title! Greve is definitely a wine-lover’s town — this is where the annual Chianti Classico is held, an annual event for vintners, experts and wine lovers. Greve in Chianti has a lot to offer foodies too: truffles are harvested in season, local salamis are well regarded, as is the local pecorino, there are local olive oil producers, and plenty of wild boar, fennel, white beans, chard and kale… There are a number of very well regarded restaurants with rooms here, several agroturismos and wine estates with accommodation — you'll find the latter around the outskirts of town. offering vineyard views, as well as incredible cellars. Greve in Chianti is quite central to the Chianti region, and while it’s large, it doesn’t feel too busy.
Radda in Chianti is a typical Tuscan town in a picturesque spot a littler higher into the Chianti region, where the hills are a bit cooler — so it’s a great base for the hottest part of summer. The wine produced here comes from some of the region’s older grape vines, and the wine production is very traditional too. History lovers may appreciate that Radda in Chianti is also known for being surrounded by the ruins of many old forts and fortifications. The town itself is old too, a warren of small piazzas and narrow medieval walkways or tunnels. As with many of the region's towns, the centres offer the more traditionally styled accommodation, and more contemporary offerings sit just outside the town walls.
Pistoia is only half an hour away from Florence, but it’s often referred to as “little Florence” because of its kindred architecture, art treasures and atmosphere. Expect Renaissance palazzos and Romanesque churches — there’s even a duomo in the historic centre of town — but without the crowds. Pistoia is also a foodie friendly pick, known especially for its chocolate production. The weekly markets on Wednesday and Saturdays bring colour and bustle to the centre of town. Accommodation-wise there's far less to choose from here than Florence, however it's also much cheaper! Here, you'll find converted palazzos and villas, guesthouses and B&Bs in town, and farmhouse conversions and resort-style hotels in the surrounding hills. Pistoia is definitely worth visiting before everyone starts hearing about it and it loses some of its charm.
Lucca’s World Heritage Listed centre is all the things you’d expect from a handsome, terracotta-coloured treasure. Expect cobbled streets opening on to charming piazzas, plenty of churches, elegant villas, art and statues, Renaissance era townhouses and city walls. Lucca also has a reputation as a spa town, and was popular in the belle époque era, including with local boy, Puccini, who performed here a lot, and is still remembered in Lucca's annual music festivals. Lucca is a lovely smaller base to consider, only a 20 minute drive from Pisa, and 45 minutes from Florence. It doesn't have a huge range of accommodation options, but you will find a lovely converted historic palazzo, several townhouses-turned-boutique-hotels, and country villas on the outskirts of town.
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Viareggio is a glamorous resort on the Tuscan Riviera. It has all the ingredients of a chic beach resort: long, sandy beaches; elegant hotels; chic beach clubs; plenty of places to eat and drink in style, and lots of sunshine! Viareggio’s beach clubs are a relatively recent addition, but some of the hotels, restaurants and bars have been part of this resort for more than a hundred years. Napoleon’s sister spent her summer here in 1882, and after that the elegant villas started springing up, followed by the fine restaurants and cafes, the galleries and museums, and the boutiques, until Viareggio was one of the most desirable places to stay on the Tyrrhenian Coast. Viareggio is a good base if you want to be close to the sea, but still want to see Pisa, Florence and Lucca — they’re all an easy day trip away. And Elba’s even closer!
Camaiore is a walled, medieval town, bordered on one side by the Apuan Alps, and on the other by the olive, wine and strawberry producing region of Versilia. It's a charming place: the streets of the centre of town are winding and cobbled, leading up to piazzas lined with Romanesque churches and medieval architecture. Plus you'll find some lovely boutiques, as well as archaeological and art museums Camaiore its a great place to come with your kids, close to the Lido de Camaiore and also not far from the beaches of Viareggio and Forte dei Marmi. There’s plenty of variety when it comes to accommodation in Camaiore, from converted villas, estates and Agriturismo to restaurants with rooms. There are also B&Bs, guesthouses and wine estates just outside town.
San Casciano in Val di Pesa is a town in the Chianti region often referred to as the gateway to Chianti, because it is the most northern town in the region, and has fantastic vineyard views. The Chianti region undulates more than the rest of Tuscany, so this is where you’ll find some of Tuscany’s most photographed roads, with their hairpin bends, that navigate around ancient hill forts, churches, hamlets, and converted farmhouses and villas. San Casciano in Val di Pesa is surrounded by 14th century walls, within which there’s a working Tuscan town, complete with friendly trattorias championing regional recipes.
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Cortona is a historic hilltop town of elegant palazzos and villas, surrounded by vineyards dotted with agritourismos, hunting lodges and wine estates. The town boasts medieval walls and stunning views of Val di Chiana. The pretty streets are filled with cafes and restaurants, and there are three museums to explore: the Accademia Etrusca, the Diocesan Museum and the Fortress of Girifalco.
