Tuscany is awash with idyllic charm – everything from the architecture to the landscape is captivating and inviting in equal measure. Choosing which typical towns and villages in Tuscany to visit on your holiday can be challenging, especially if you want to stay off the beaten track.
The best way to explore is by car. Driving around this gorgeous region is a revelation, and a great way to see as much as possible from your villa in Tuscany. We’ve researched some of the most authentic and beautiful towns and villages in Tuscany to give you a real taste of ‘vita Italiana’. Medieval histories, walled towns and renaissance stylings await.
Beautiful Tuscan Towns to Visit
In the southern Tuscan province of Arezzo, Cortona is a traditional walled Etruscan town. Sitting at about 600 metres above sea level, it offers spectacular views over the surrounding valley and Lake Trasimeno. Although the town is small, it’s packed with interesting sites to visit – such as the Diocesan Museum, where you’ll find a beautiful panel painting by Beato Angelico; and the MAEC, which holds fascinating artefacts found in surrounding archaeological sites. Beautiful churches, like the Santa Margherita Sanctuary, are strewn around the town and well worth an explore. You may recognise it from the book and film, Under the Tuscan Sun. In this region, famed for its red wine – you will not be short of places to relax and enjoy a drink after a day of sightseeing. Find your way around Cortona!
Where to stay: Le Celle
Located a stone’s throw from Siena, Montepulciano is a feast for the senses. Renaissance architecture fills this medieval town, brought about by the affluent Medici family in the 16th century. So genuine is its architecture, that no major building work has happened here since 1580. The heart of the town lies in the Piazza Grande, where you can enjoy a glass of local Nobile wine and admire the rough brick exterior of the Duomo. If that first glass has whet your whistle, there are a myriad of cellars and tastings to experience around the square.
Make sure to bring with you this useful map of the best ten Tuscan wineries and start ticking them off!
Where to stay: Casale Cocca
Lucca sits on the Serchio river, making it one of the few Tuscan towns and villages that does not occupy a hilltop position. It does have the traditional renaissance town walls… but takes them to the next level. They are treelined and popular for strolling and cycling along, providing a wonderful vantage point to admire the town’s cobbled streets and beautiful buildings. The streets all merge in the middle to create the perfectly circular Piazza dell’Anfiteatro, which is lined with pretty shops, bars and restaurants. Lucca is famous for being the birthplace of Puccini, and visitors during their villa holiday in Tuscany can enjoy concert recitals most evenings in the atmospheric Church of San Giovanni. Plan your trip!
Where to stay: Villa i Grilli
Known as “Little Jerusalem”, this small Tuscan town is in the beautiful region of Maremma near the coast. Tiered, tile-roofed buildings sit on top of layers of red volcanic “tufa” stone, giving this beautiful hilltop town a distinct look. Unusually, for historically Christian Italy, Jews were able to live in Pitigliano peacefully right up until 1622. You can learn more about the town’s Jewish history in the Jewish Museum of Culture, and sample some local Jewish delicacies, “Sfratti”. These are stick-shaped biscuits filled with ground walnuts, honey, nutmeg, orange peel and wrapped in dough. And were apparently invented by the Jewish community as a result of police hitting them with sticks to force them into the ghetto.
You should also be sure to visit the underground tunnels and caves dug into the tufa beneath the city, during your villa holiday in Tuscany. This labyrinth of passages and rooms has been in use since Etruscan times. Ask at the tourist office for details on when they are open to the public.
Where to stay: Villa Volsini
Most Beautiful Villages in Tuscany
Sleepy Barga is in the Garfagnana region, close to the more well-known town of Lucca. This hidden ancient village in Tuscany is a rabbit-warren of very narrow cobbled streets, tiny squares, and steep staircases. The Duomo in the centre is ancient and beautiful and provides panoramic views. Practically untouched by tourism, Barga is perfect for soaking up the true region during your villa holiday in Tuscany, undisturbed by tourists. This will mean brushing up on your Italian before you go though! Plan your trip ahead!
High in the steeper terrain of Northern Tuscany lies the enigmatic commune of Fosdinovo. It is dominated by the brooding Castello, which dates back to the 12th century, and now holds a museum and cultural centre that you can visit. As well as walk around the remarkably well-preserved structure.
The full-circle view afforded from Fosdinovo’s hill-top location is remarkable. On clear days you can see all the way to the coast with the island beyond, and the spectacular vista of mountains that, legend has it, inspired Dante’s Inferno. Charming narrow streets snake through the village, leading you to Piazza Garibaldi – an ideal square to watch the world go by and admire the setting.
The ancient Tuscan village of Collodi is well worth a visit, and that’s no word of a lie! Most famous for being the birthplace of beloved children’s character, Pinocchio, this narrow fairytale village cascades down a hillside in central Tuscany between Florence and Pisa. This is a perfect Tuscan experience for storybook fans, and the dedicated park shouldn’t be missed. The Park of Pinocchio captures the imagination with bronze sculptures set among beautiful gardens, mazes and fountains. Collodi is also home to the villa and gardens of Garzoni, a beautiful example of Italian Renaissance design.
8. San Gimignano
The most well-known Tuscan village on our list, this one may be bordering on town status, but San Gimignano started life in the 1150s as an Etruscan village. Today, the 14 towers of this Medieval walled community provide an understandable draw for tourists seeking history, atmosphere and a taste of the rural Italy of old. Several museums and galleries make this a varied and cultural village to visit in Tuscany. Find out more here!
Where to stay: Lorenzo Village
The tiny hamlet of Monteriggioni, near Siena, is uniquely fun to say, but that’s not all. It may be tiny, but this ancient Tuscan village packs a punch. The entire place is hidden inside a fortified citadel, whose walls and 14 towers conceal its existence entirely. Nowadays only a few of the buildings are lived in. The rest of the village is given up to an interesting museum housing Renaissance armour and artifacts, along with a few shops and restaurants. The medieval festival held here in the first two weeks of July is a wonderful time to take your villa holiday in Tuscany.
If you’re feeling inspired to explore this historic and famously beautiful region of Italy, there’s surely no better way to soak up the atmosphere than from your own villa to rent in Tuscany with Oliver’s Travels. We’ve got a rundown of the best swimming pools, and the best family friendly villas in Tuscany to help you to get the most out of your holiday.
If you’re already in the process of planning your trip and in need of some advice, give our concierge team a call, they’ll be happy to chat.