The 5 Most Beautiful Towns and Villages in Tuscany

Endless green hills, sun-drenched vineyards, cypress-lined lanes and fairytale towns where traditional trattorias and fresco-filled churches sit side by side - there are few places in the world quite like Tuscany. Rich in history, charm and beauty, it's a region that's so easy to fall in love with.

Although Florence often steals the spotlight with its skyline-piercing Duomo and Renaissance masterpieces, venture beyond the city and you'll discover some of Italy's most beautiful destinations. From hidden hilltop villages to ancient towns, these places offer an authentic taste of Tuscan life.

San Gimignano

Nestled in the heart of Tuscany, Sam Gimignano is one of the region's most popular towns. But don't let its popularity put you off, as there's a reason it's so loved. The town is absolutely stunning, with atmospheric cobbled streets that lead to lively piazzas, medieval stone towers that serve up countryside views and ancient walls that transport you back in time.

There are two main streets in the UNESCO-listed historic centre - Via San Giovanni and Via San Matteo – both lined with cafes, trattorias and artisan shops selling everything from hand-painted ceramics to locally crafted leather goods. Make your way up either street and you'll find yourself at Piazza del Duomo, the heart of San Gimignano. Take a seat on the steps and watch the world go by and admire some of the town's most famous landmarks including the Duomo of San Gimignano and the Palazzo Comunale.

For panoramic views, make sure you climb to the top of Torre Grossa, the tallest of San Gimignano's medieval towers, where you'll be rewarded panoramas of the rolling Tuscan hills. The town is also home to some beautiful churches such as San Lorenzo in Ponte and and Chiesa di Sant’Agostino – make sure you peek inside to see the amazing interiors and artwork.

Our tip: enjoy a scoop (or two) of the amazing ice cream at the award-winning Gelateria Dondoli in Piazza della Cisterna. There's usually a queue but it's well worth it.

Montepulciano

Perched above the rolling valleys of Val d'Orcia and Val di Chiana, Montepulciano’s location is at picture-perfect as it gets. But stunning views aren't all the town has to offer. Montepulciano is a blend of winding cobblestone alleys, Renaissance palaces, beautiful churches and buzzing piazzas that make it a dream to explore.

The town is actually most famous for its wine - Vino Nobile di Montepulciano is one of the country’s most prestigious reds. And what better place to try it than in the town itself – pull up a chair in one of the enotecas that line the streets or head underground to tour the town’s famous wine cellars and learn all about the local tipple. 

The above is, of course, best done after exploring Montepulciano. Porta al Prato, a medieval gate, is the town’s grand entrance – wander through to reach the main street, a steep and winding alley packed with charming wine bars, artisan shops, trattorias and shops selling local produce, from olive oil to honey and pastas. Stop at one of the cafés or trattorias along the way to catch your breath and tuck into local specialities like pici, thick, hand-rolled pasta.

The main street will eventually lead to Piazza Grande, the centre of the town. It’s here you’ll find the The Cathedral of Santa Maria Assunta (Duomo) and a number of beautiful palaces. A visit to the town hall, Palazzo Comunale is a must – you can climb its medieval tower for the most beautiful views of the valley below.

Our tip: Enjoy a wine tasting experience at De'Ricci Cantine Storiche. Take a tour of the historic cellar before sampling a variety of local wines and Tuscan produce.

San Qurico d’Orcia

A small hilltop village in the heart of the Val d’Orcia, San Quirico d'Orcia is one of the best places to visit for an authentic Tuscan experience. It still feels like a hidden gem, with less crowds than many of the region's more famous towns and villages. However, it's still every bit as beautiful, with medieval architecture, historic churches and the most picture-perfect views.

Via Dante Alighieri is the main street running through the village – stroll along and experience local life, admiring the beautiful architecture as you go. The main square, Piazza dell Liberta, sits at the heart of village, surrounded by cafes where you can enjoy a gelato, a lazy lunch or an aperitivo. 

From here, you can also wander into the Horti Leonini Gardens. These formal Renaissance gardens are beautiful with perfectly manicured hedges, elegant statues and cypress trees, creating a lovely setting for a peaceful stroll. There are also two main churches in the village that are also well worth a visit; Chiesa di San Francesco, located just off the main square, and Collegiata di San Quirico d'Orcia a little futher along – make sure you go inside to witness the stunning interiors.

Our tip: Stop at Poggio Covilli Farmhouse on your way to San Quirico d’Orcia. This cypress-lined driveway is the perfect place to get a typical Tuscan photo and soak up the gorgeous views.

Pienza

Located only around 9 miles from Montepulciano, Pienza is another one of Tuscany's most beautiful towns. In the 15th century, Pienza was completely redesigned by Pope Pius II into the perfect Renaissance town, which is evident today in the elegant architecture, charming streets and beautiful piazzas throughout the town.

The centre is compact, with Piazza Pio II sitting at its heart. Lining the piazza are some of Pienza’s most important sights including the Duomo di Santa Maria Assunta, a beautiful 15th century cathedral, Palazzo Piccolomini, the Pope’s former residence, Palazzo Comunale, the town hall of Pienza, and Palazzo Borgia, home to the Diocesan museum where you can browse a collection of modern and medieval works of art.

Beyond its history and architecture, Pienza is also famous for its pecorino cheese. You can sample the local speciality at one of the many shops throughout the historic centre. If you visit during the first week of September, you can even enjoy the town's annual pecorino cheese festival!

Our tip: Take a walk along Via del Casello for some of the most beautiful views of the surrounding Val d'Orcia countryside.

Volterra

Another beautiful Tuscan town, Volterra sits on a hilltop between the Era and Cecina valleys. Known for its Etruscan roots and amazing medieval architecture, the town is a dream for history lovers. Explore the Fortezza Medicea, a 15th-century castle overlooking the town, and visit the ancient Roman Theatre, which is said to be one of Italy’s best-preserved theatres.

Although just a simple stroll around the town will transport you back in time, with landmarks such as Palazzo dei Priori, the town hall dating back to the 13th century and considered the oldest in Tuscany, and the Cathedral of Santa Maria Assunta, with its Romanesque exterior and Renaissance interior. You can also delve more into the town’s Etruscan roots at the Museo Etrusco.

Volterra is also famous for its alabaster craftsmanship, a tradition that dates back more than 2000 years and is still very much alive today. Wander through the atmospheric streets and you’re guaranteed to stumble across workshops where you can see unique creations.

Along the town’s charming streets, you’ll also find plenty of cafés and restaurants serving traditional Tuscan cuisine, alongside salumerias and quaint souvenir shops. It’s the perfect place to have a wander and soak up the authentic Tuscan atmosphere.

Our tip: Climb the steps of Palazzo dei Priori (the town hall) for some of the best views in Volterra.

Whether you fancy sipping wine in Montepulciano or sampling pecorino in Pienza, Tuscany is full of unforgettable experiences. Head to our blog or Instagram for more travel inspiration.