From 12th-century UNESCO World Heritage sites to small towns deep in the Tuscan countryside, these are the most beautiful towns in Tuscany.
When you picture the Italian province of Tuscany, you probably imagine long rows of grapevines stitched into endless rolling hills, small towns of red-tiled rooftops framed by graceful poplars, languid sunsets, and delicious local food and wine on outdoor tables.
And it’s no wonder we all have this dreamy image in our heads! Tuscany has captivated artists, writers, musicians and dreamers for centuries. As well as its famous cities such as Pisa, with its leaning tower, and Florence’s iconic Duomo, Tuscany is loaded with villages and small towns that epitomise our romantic notions. There’s even the spectacular island of Elba, for a magical slice of Tuscan paradise.
So, if you’re ready to live your very own Tuscan dream, come along with me as we wander through the Tuscan countryside and explore some of the most beautiful towns and villages in Tuscany.
Also, if you want to plan a trip to remember, don’t miss my guide to the best vineyard hotels in Tuscany. They offer the quintessential Tuscan experience.
13 Most Beautiful Towns and Villages in Tuscany, Italy
San Gimignano
Established in the 12th century, this small walled town is also known as The Town of Fine Towers. From the surrounding landscape of vineyards and olive groves, you walk up through tired streets of red-tiled houses to the Pallazo Comunale. Here you’ll find the fourteen tower houses, the most impressive of which is the 54-metre-high Torre Grossa.
Down in the Piazza della Cisterna, you can grab a gelato from the world-famous Dondoli Gelateria then find a shady spot for an afternoon riposo (the Italian word for snooze).
To make things nice and simple, you can visit on a day trip from Florence with GetYourGuide.
Panzano
Located halfway between Florence and Sienna, Panzano lies in the heart of the Chianti wine-growing region. This charming hilltop village has an encircling wall from which you can gaze out across the neat vineyards beneath the blue Tuscan sky.
May to September is the best time to visit the Chianti Region with the rainy months being April and October. Although, if you do happen to visit during winter, you might be lucky enough to see Panzano dusted with snow – a truly beautiful sight!
The narrow streets of the car-free Old Town are crammed with colourful shops and wine bars (of course) and lead up to the Church of Santa Maria Assunta, which dominates the skyline of Panzano. Stop for a coffee at Il Vinaio where you’ll sit beneath trellises of grapevines with a view out over the valley.
Pienza
Perched atop a hill overlooking the scenic Val d’Orcia, this Tuscan village was rebuilt in the 15th century by Pope Pius II as an “ideal town.” Pienza was added to the list of UNESCO World Heritage sites in 2004 and it’s easy to see why.
The Renaissance architecture blends into the landscape and every turn (you can walk right around the village on its encircling bastion walls) produces a dream vista of the surrounding countryside. If you’re into photography, you’ll love Pienza! You won’t stop snapping!
Foodies will also love Pienza. The local pecorino cheese can be savoured in dishes served in the many little eateries dotted through the town’s alleys and cobbled piazzas. Plus, there’s even something for movie buffs: the final scene from Gladiator was filmed in the countryside near Pienza! How cool is that?
Florence
OK…I know that Florence is really a city, but it does feel more like a collection of Tuscan villages when you’re there! Besides, it’s a great starting point for any visit to the region.
The narrow streets around Piazza della Signoria radiate out in all directions and you can see the Palazzo Vecchio, the Piazza del Duomo and the Uffizi Gallery in the same area. From there, anything is possible. So grab a map of Tuscany, take a seat at one of the many cafés, and plot your route through the Tuscan countryside.
Monteriggioni
This is surely one of the most beautiful places in Tuscany… if not all of Italy! The walled village looks more like a movie set than a real place. It reminds me of some of the spectacular hilltop villages in Italy’s Marche region.
Monteriggioni’s fourteen square towers, set at intervals around its encircling fortified wall, dominate the enchanting local landscape of vineyards and hazy pastel hills.
The lovely 13th-century church of Santa Maria Assunta dominates the centre of the village and you’ll find a perfect place to sit and people-watch at one of the cafés in the Piazza Roma.
Monteriggioni is a popular day trip from either Sienna or Florence and you can combine a visit to the village with wine-tasting on a tour with GetYourGuide.
Pitigliano
Nicknamed “Little Jerusalem”, this Tuscan town was originally established as a haven for Jews escaping persecution in Rome. Built on a rocky hilltop overlooking the Fiora Valley, Pitigliano offers a wonderful mixture of traditional Tuscan architecture and unusual houses carved into the soft volcanic tufa rock.
One of my favourite things about Pitigliano is the food. A local speciality is known as sfratti which is a stick-shaped biscuit filled with ground nuts, honey, nutmeg and orange peel. These are delicious, often enjoyed with either with coffee in the morning or (even better) with a glass of the local Bianco di Pitigliano wine in the evening!
Cortona
If you’ve ever seen the movie Under the Tuscan Sun you’ll be familiar with Cortona. Easily reached as a day trip from Florence or Sienna, Cortona is one of the most beautiful places in Tuscany.
Despite the tourist crowds, this ancient hilltop town still manages to feel laid back and authentic.
The narrow medieval streets around the Palazzo Comunale are fascinating places to wander. There are plenty of eateries to choose from and I recommend you try the local Tuscan delicacy called Ribollita: an earthy bread soup made with white wine and fresh locally-grown beans. It’s hearty and delicious!
The Santa Margherita Sanctuary is a small basilica just outside town. The church was built to house relics of the 13th-century saint Margherita de Cortana, whose incorrupt body is on display beside the main altar. It’s an odd, yet strangely compelling thing to see (you might even say ghoulish!) but the interior of the church is richly decorated and the place has a quiet, rural feel.
Montepulciano
Time really has stood still in this gorgeous hilltop village, an easy day trip from Siena. The affluent Medici family established Montepulciano in the 16th century and no major building work has been done here since then!
At the centre of the village lies the Piazza Grande, lined with restaurants and wine shops where you can sample the famous Vino Nobile vintages.
Collodi
We all know the story of Pinocchio, the wooden boy who came to life and couldn’t lie. Well, I’m not going to lie… Collodi (which was home to the author who created the timber boy) really is one of the most beautiful villages in Tuscany!
You’ll see houses cascading down a tree-clad hill below the ancient church of San Bartolomeo, from where you have a panoramic view of the surrounding countryside.
The Italian Gardens at the Villa Garzoni feature grottos, statues, a bamboo forest and wandering peacocks. The father of Carlo Collodi, who wrote Pinocchio, was the gardener at the Villa Garzoni (although I don’t think his name was Geppetto!!)
The Butterly House is another of Collodi’s unique attractions, containing over 1,000 butterflies from all over the world, housed inside a glass and stone greenhouse.
Casale Marritimo
The brick houses of this lovely village, not far from the coast of the Tyrrhenian Sea, climb over a low hill with vineyards running right up to its edges. The arched pathways, cosy cobbled courtyards and medieval walls provide almost unlimited opportunities for photographers to frame shots of the surrounding landscape.
This is a village where you can simply laze about, drinking coffee in the piazzas and browsing the little shops and galleries. To me, Casale Marritimo epitomises Tuscan village life. Sure, there are historic churches and Etruscan ruins nearby, but the best thing about this lovely little town is that you can do nothing and not feel guilty. Sometimes that’s the best part of travelling!
Barga
Located in the valley of the Serchio River, Barga is oddly known as “The Most Scottish Town in Italy” because around 40% of its residents have Scottish ancestry. So, if you are hankering for a glass of whisky and some haggis during your travels, this is the best town in Tuscany to find a wee dram! There’s also an incongruous red phone box which operates as a book exchange!
But Barga certainly doesn’t look very Scottish. Its lovely limestone buildings, capped with roofs of red tiles, give it a classic Tuscan feel. Its striking Romanesque cathedral — the Collegiata di San Christoforo — contains frescoes and sculptures dating back to the 11th century. Barga is also famed for its arty side, with several annual opera and jazz festivals throughout the year and a sizeable population of artists and writers.
The town’s rural location, surrounded by a verdant landscape of forests and vineyards backed by ranges of hills, gives it a fresh, alpine feel. It’s a lovely contrast if you’ve been spending lots of time in Italian cities.
Sansepolcro
Famous as the birthplace of the Renaissance artist Piero della Francesca, Sansepolcro is an art lover’s town. The Museo Civico houses work by Santi di Tito, and Luca Signorelli as well as Francesca’s masterpieceThe Resurrection.
Wandering around Sansepolcro, you soon forget that you’re actually in a fairly large manufacturing town. Away from the industrial area, the quiet cobbled lands and piazzas are full of interesting churches, chapels, shops, and houses.
There is the cathedral of San Giovanni Evangelista with its arched cloisters and the small but perfect Church of San Lorenzo with evocative paintings by Rosso Florentino.
When your tire of churches, chapels and piazzas (as if you ever could!) there are plenty of great places to chill out with a delicious Italian snack or aperitif.
Lucca
I might have saved one of the best ’til last! To me, this lovely valley town beside the Serchio River, with its encircling stone wall and tiny tree-hung piazzas, is one of the most beautiful places in Tuscany… no wait, maybe all of Italy.
If you’re a walker (or a runner) Lucca’s walls are a superb circular walk with views out across the town’s rooftops to the distant Apuan Alps. You can also hire bikes to explore the town centre or if you feel like venturing further afield.
Lucca is another Tuscan town where you can while away days people watching, soaking up the relaxed Tuscan lifestyle and relaxing.
And after a hard day of relaxation, you can head down to the bars and cafés of the Piazza San Michele for drinks and nibbles. One of the most popular places here is Enoteca Marsili, where you sit outside beneath the flower-draped balcony and dine the evening away.
Every time I travel to Italy I’m excited to venture away from the bigger cities. When it comes to Tuscany, there’s something captivating about its beautiful towns and villages dotted throughout the perfect countryside. Don’t forget, if you’re looking for dreamy places to stay, I’d recommend these charming vineyard hotels.
Trying to plan your holiday in Italy, but need a little more help? Don’t miss these posts:
- 13 Most Beautiful Towns and Villages in Tuscany, Italy
- 13 Best Vineyard Hotels in Tuscany, Italy
- Where To Stay In Elba, Italy – The 15 Very Best Hotels In Elba
- The Ultimate Italy Honeymoon Itinerary
- The Ultimate Italy Road Trip Itineraries
- The Ultimate Southern Italy Road Trip
- The Ultimate Northern Italy Road Trip