Best towns in Tuscany – 12 towns of Tuscany not to be missed

Tuscany is an Italian region full of charm and diversity with its beaches, mountains, hills and towns. Everything from the architecture to the landscape is absolutely stunning. 

The towns and villages of Tuscany are surely one of the most appreciated sights of this region. But which of the villages should you include in your itinerary?

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Choosing the nicest towns to visit in Tuscany on your holiday can be challenging, especially if you want to stay off the beaten path. But worry not, because I have traveled around Tuscany many times and visited most of the towns multiple times.

To help you make your choice, I’ve put together a list of the most authentic and beautiful villages. Below I’ll be sharing the best towns to visit in Tuscany including key insights about them to give you a real taste of Tuscany.

This list does not include major cities in Tuscany as the real experience lies in visiting smaller towns and making authentic experiences.

Best Historic Towns of Tuscany

When it comes to Tuscany, it’s no wonder its towns come with a rich Medieval and Etruscan history. Below I’ve listed the best Tuscan towns to visit known for their rich history and stunning architecture.

1. San Gimignano

San Gimignano is a town not to be missed! This picturesque hilltop town in the heart of Tuscany between Siena and Florence is one of the most interesting towns of the region.

San Gimignano can be considered one of the best-preserved medieval towns of all Italy. Due to its high medieval towers, it has earned the nickname “Tuscan Manhattan” for its appearance.

San Gimignano was also known to be a stop for pilgrims walking to Rome and still is a beautiful part of the Via Francigena hike. 

Best things to do in San Gimignano

1. Explore the historical center starting at Piazza della Cisterna
2. Climb the Medieval towers, especially Torre Grossa
3. Visit and learn about the town’s history at the Civic Museum
4. Head to the Collegiata also known as Church of Sant’Agostino
5. Go on a truffle hunt and lunch experience

2. Siena 

Siena is the largest among the Tuscany towns scattered among the hills, located just 75 km south of Florence. It is in fact a medieval town with the dimensions of a city that has not been touched by industrial development. 

Siena’s historic center was declared Unesco Heritage and with its ancient history, charming streets, stunning architecture, and mouthwatering cuisine, Siena is a must-visit destination and one of the best cities to stay in Tuscany. I’ve come back here multiple times and the Siena Cathedral is my favorite in Italy!

Siena is also well known for the Palio, a horse race held in July and August in Piazza del Campo. Ten horses and riders compete, each representing their contrada, or neighborhood.

Best things to do in Siena

1. Visit the Duomo Complex and climb the Facciatone with this skip the line ticket 
2. Climb Torre del Mangia 
3. Wander the streets of the old town around Piazza del Campo on this walking tour 
4. Watch the sunset from Orto dei Tolomei

3. Pitigliano 

Pitigliano is located at the border of Lazio and Tuscany and , perched atop a large tufa hill.

The streets in Pitigliano are paved with cobblestones and lined with archways and cascades of bright purple bougainvillea, making the city center a magical place to wander around.

The town is well-known for its synagogues and ancient stairways that lead to them. Indeed, Pitigliano is one of the towns in Tuscany where Etruscan culture is particularly evident. I remember being very impressed learning about the history and walking among Etruscan tombs and caves!

For the ultimate experience, time your visit to match with one of the traditional festivals held in Piazza Garibaldi.

Best things to do in Pitigliano

1. Stroll through the historic city center on this private walking tour
2. Walk the Via delle cave Etrusche
3. Visit the Jewish Ghetto, theSynagogue and museum
4. See the acquedotto Mediceo, an ancient waterway

4. Cortona

Cortona is one of the most beautiful hill towns in Tuscany, perched on the hillsides of the pre-Apennines and crowned with an imposing medieval tower. This charming village is perfect for wandering, with its pretty, winding alleyways adorned with washing lines and hanging baskets of flowers. 

Cortona’s elevated location offers a splendid vantage point over the Chiana Valley, providing some of the best panoramas and views, including a distant glimpse of Lago Trasimeno.

Watching the sunset while sipping some red wine in Piazza Garibaldi is one of my favorite memories from my trip around the Tuscan hills.

The weekend markets are a must-see experience and perfect for indulging in local red wines and lampredotto sandwiches (slow-cooked cow stomach served in a crusty bread roll) while browsing for artisan crafts.

Best things to do in Cortona

1. Stroll through the historic town center, I recommend this walking tour
2. Visit the Etruscan Museum
3. Visit Fortezza di Girifalco e Basilica di Santa Margherita
4. Explore the archeological park of Sodo
5. See the Palazzo Comunale

Best Hill Towns of Tuscany

Nestled amidst the rolling hills of Tuscany, the region’s best hill towns are characterized by winding cobbled streets, medieval architecture, and breathtaking panoramic views. 

5. Montepulciano

Located near Siena and Pienza, Montepulciano is a town that has it all and it is in my opinion one of the nicest towns in Tuscany. I also believe it is the best area to stay in Tuscany if you are planning to visit more of the region. 

Montepulciano is built on a hill and has wonderful views of the Tuscan countryside. The medieval town is filled with clean architecture. Its heart lies in Piazza Grande, where you can enjoy a glass of local delicious wine and admire the majestic Duomo. 

In fact Montepulciano is very well known for its wineries and wines making it the perfect destination for wine tasting. I highly recommend this wine tasting tour.

Best things to do in Montepulciano

1. Visit Palazzo Comunale in Piazza Grande, join this private walking tour
2. Take a stroll along il Corso, Montepulciano main street
3. Tour the historical cellars of Montepulciano 
4. Visit the suggestive Tempio di San Biagio
5. Enjoy a sunrise balloon ride over the Tuscan hills

6. Montalcino 

Montalcino is one of the best hilltop towns in Tuscany located close to Montepulciano in the Crete Senesi area in Val d’Orcia.

It is enclosed by huge 13th-century defensive walls which make it a very striking sight. It also  has a perfectly preserved castle and fortress that have remained unchanged over the years.

Montalcino is a special destination for wine lovers, offering opportunities for wine and food tasting in excellent cantinas.

Best things to do in Montalcino

1. Visit the Fortress and climb its walls
2. Stroll through the city center, I suggest this private city tour
3. Take the Nature (steam) Train to the countryside
4. Visit one of the many wineries and cantinas, I suggest this winery tour

7. Pienza 

Pienza is a tiny Renaissance gem located in Val d’Orcia, near Montepulciano and Montalcino, in southern Tuscany. It is the best village in Tuscany in my opinion. 

It was designed by Pope Pio II as an unusual urban project as he refurbished his hometown and revived its exquisite Renaissance architecture.

Designated as a UNESCO World Heritage site, wandering its streets really feels like you are in a utopian village and it actually is one of my favorite Tuscan villages, its vibes are unmatched!

Best things to do in Pienza

1. Stroll through the village and the Bastions of the Village walls, I recommend this private walking tour
2. Visit Palazzo Piccolomini
3. Visit the Cathedral and Palazzo Pio II
4. Try Pecorino di Pienza, a typical sheep cheese produced in town

8. San Quirico d’Orcia

San Quirico d’Orcia is definitely my favorite village among the hills and the best place to visit in Tuscany if you love good views! It’s very underrated but its location makes it a must-see. 

Built on top of a hill in Val d’Orcia, San Quirico d’Orcia was a popular stop for pilgrims and still is part of the Via Francigena hike.

The village itself is very tiny but its surroundings are the best of Tuscany in my opinion.

Best things to do in San Quirico d’Orcia

1. Stroll through town and visit Collegiata di San Quirico
2. Visit the gardens Orti Leonini
3. Go see the famous Cypress trees on the nearby hill
4. Head to the Gladiator’s set at the Terrapille Farm road

9. Bagno Vignoni

Lesser known and a true hidden gem, Bagno Vignoni is a thermal resort in Tuscany with a unique charm.

The main square of the village is almost entirely occupied by a natural hot water basin of ancient origin. Around the basin stand traditional stone houses that have a rustic yet romantic appearance and are the perfect location for many cute restaurants and bars. 

It is not possible to bathe in the basin of the central square, but you can find natural hot springs nearby, Bagni San Filippo is the best one. I’ve spent one entire morning there having the pools almost all to myself as it’s still a hidden gem.

Also, following the flow of water from the central basin, you can reach the Parco dei Mulini, a complex of ancient mills and gorges.

Best things to do in Bagno Vignoni

1. Visit the historic center and Piazza delle Sorgenti
2. Explore Parco dei Mulini
3. Visit Chiesa di San Giovanni Battista
4. Head to Bagni San Filippo for the best natural hot springs
5. Take a day trip to Terme di Saturnia

Best beach and seaside towns in Tuscany

Basking along the azure shores of the Mediterranean, Tuscany’s seaside towns are a picturesque blend of sun-kissed beaches, vibrant harbors, and seafood cuisine.

10. Viareggio 

Popular among locals, the gorgeous town of Viareggio has always been one of the best coastal towns in Tuscany. This town is known throughout Italy not only for its fine white sandy beaches but also for its Carnival, one of the most important and biggest in the country. 

Viareggio is perfect to relax in the sun on the Versilia coast or dine at sunset on the lungomare. But also to enjoy the nightlife, as it is famous for its bars, nightclubs, beach parties, and aperitif-based social scene. 

Best things to do in Viareggio

1. Stroll through Lungomare di Viareggio
2. Relax at Spiaggia della Lecciona
3. Visit Palazzo delle Muse and its art gallery of modern art
4. Visit the citadel and museum of Carnival or even better attend the Carnival parade in February 
5. Explore Pineta di Ponenete

11. Portoferraio – Isola d’Elba

If you are looking for the perfect island getaway, Isola d’Elba is perfect for you, and you cannot miss visiting Portoferraio! After all, this is likely where you will disembark from the ferry and it is one of the best towns of the island.

Overlooking the northern coast of Elba, it serves as its capital and at the same time is the main port and the most populous municipality. Portoferraio has an exquisite medieval historic center as well as gorgeous beaches and sea.

Even its name hides the essence of the Island of Elba: the words ‘port’ and ‘iron’ have been shaping the history of this beautiful island for centuries.

Best things to do in Portoferraio

1. Explore and relax at the best beaches of the Island: Spiaggia delle Ghiaie and Spiaggia di Capo Bianco
2. Visit the fortresses that encloses the historic center
3. Visit the Duomo
4. Explore the coast on this full day kayak tour 

12. Castiglione della Pescaia

Castiglione della Pescaia is one of the prettiest towns in Tuscany. Located in the area of Maremma Grossetana. It has it all and satisfies lovers of both ancient villages and beach holidays.

The historical center is a charming medieval village perched atop Monte Petriccio. It features medieval walls, towers, a castle, picturesque alleys, and breathtaking panoramic views.

At the foot of the hill lies the coastal area with stunning beaches, a promenade, a fishing port, and a marina where you can rent a private boat to explore the islands of Elba, Capraia, and Giglio. This area is also rich in nightlife. 

Overall, Castiglione della Pescaia is one of the best destinations for a well-rounded holiday, offering a perfect blend of culture, nature, and beach life.

Best things to do in Pescaia

1. Visit the medieval Castle
2. Stroll along the Lungomare
3. Explore the natural reserve of Diaccia Botrona, I recommend this bird watching and photography tour for the best chance at seeing flamingos
4. Relax at Spiaggia Rocchette