If you are planning a visit to Tuscany, you’re sure to have noticed the abundance of Tuscan hill towns in Italy: small, quaint towns, usually with walls, located on hilltops. But there are so many, each with a unique piazza, church, and a mix of museums… how can you possibly choose?

We present: are our top selections for Tuscan hill towns to visit, and well as the key or defining features you’ll experience during a visit! These towns are located in a variety of locations within Tuscany – some on the coast, some in National Park forests, some close to larger cities. We hope that this guide will help you to narrow down your choices. 

These towns are most easily traveled by car, but you can also make a hike out of them if you’re in for an adventure and traveling when the weather is agreeable. As you explore the options, consider both which attractions pique your interest, as well as their relative locations.

Let’s take a look!

1. Pienza

The green landscape of a Tuscan hill town with a view of cultural structures and houses
Pienza is a typical Tuscan hill town

Famous for its revitalization by Pope Pius II as the “idealized” city of Italian Renaissance urban planning, the Tuscan hill town of Pienza was originally a small village called Corsignano before being revitalized and renamed by the Pope himself. Pienza is also known for its brand of Pecorino sheep’s cheese. 

Travel Secret: If you’re a foodie, visit the first weekend of September, when the town hosts a traditional celebration of food, or sagra, called Fiera del Cacio. The celebration is dedicated to Pecorino and other traditional foods. Be sure to catch the cheese rolling competition!

2. Pitigliano

Pitigliano is an ancient medieval town on a cliff of the mountain.
Pitigliano is an ancient medieval town very famous in the world, which is located on a Tuscan hill

One of Southern Tuscany’s best kept secrets, the hill town of Pitigliano is dubbed the “Città del Tufo” for its quality of being built on Tufa rock. Known as “Little Jerusalem,” Pitigliano has a rich Jewish history with origins in the 15th century, though its community was threatened by the racial laws of Italian fascism and many people fled or went into hiding. Today visitors can visit the Museum of Jewish Culture and the Pitigliano Synagogue.

Travel Secret: Don’t skip Vie Cave if you enjoy the outdoors – this path is lined with caves and Etruscan ruins.

3. San Gimignano 

Afternoon view of beautiful landscape with a view of the castle  in San Gimignano, Tuscany
The town of San Gimignano is a typical Tuscan hill town

San Gimignano delle Belle Torri or San Gimignano of the Beautiful Towers, offers an unforgettable Tuscan hill town skyline: amidst all the hilltop towns, it is unique for the 14 towers etched across its cityscape. This UNESCO World Heritage Site was one home to as many as 72 towers, which reached as tall as 50 meters into the air and were built as a display of power. 

Travel Secret: Don’t miss the opportunity to visit the Torre Grossa, the tallest town in the town. Built in the 13th century, it offers a stunning view of the city and surrounding landscape from above! Tickets can be purchased from the Civic Museum

Explore More: San Gimignano and other interesting Tuscan towns 

4. Massa Marittima

Tourist visit the hilltop town of Massa Marittima, Tuscany.
Massa Marittima is located at the top of a Tuscan hill

The hilltop town of Massa Marittima has everything: a stunning duomo, a charming centro storico or historic center, a clock town you can climb into, and a number of museums. 

Make sure to find the famed public fountain (connected to the city aqueduct) known as “The Source of Abundance,” where a 13th-century fresco was discovered in the late 1990s. Dubbed “The Tree of Fertility,” it depicts a tree with phallic symbols hanging from its branches, and a group of women conversing and working below. There are two theories about its origins: either it offers an omen related to water as an ancient symbol related to the nature of male fertility, or served as a politico manifesto from the government warning of the witchcraft, sterility, and famine that would occur if the city reverted to its previous rulers. 

Travel Secret: Only five kilometers outside of town, you can also access the Lago dell’Accesa Archaeological Park, located beautifully on the perimeter of a small lake. 

5. Bolgheri

Nighttime view of the historic town with famous wines tasting in Bolgheri.
Bolgheri is located along the Tuscan coast and is a destination worth seeing

Famed for its tradition-surpassing Super Tuscan wines, Bolgheri is a popular stop on the wine coast of Tuscany. Here, you’ll have a chance to visit vineyards for tours or dining. The town itself also offers an abundance of opportunities to experience these special wines, as well as local olive oil and other artisan products. 

Travel Secret: Bolgheri is home of the famous cypress-lined road called Viale dei Cipressi, which leads from the historic center of town to the small church Oratory of San Guido.

6. Montepulciano

Montepulciano is a hilltop town with an old structure and delicious wines located in Tuscany.
Montepulciano is a hilly town located in Tuscany

Another wine-specialized Tuscan hill town, Montepulciano is home to the famed Vino Nobile di Montepulciano. The Piazza Grande, the highest point in the town, is also known as a location from the Twilight movies. The main street, Il Corso, will lead you through the old town and its many delicious restaurants and cafes. 

Travel Secret: If you visit the last Sunday of August, you’ll find the Bravio delle Botti – a wine barrel race through town, completed by two men from each contrade or neighborhood of Montepulciano.

7. Castiglione della Pescaia

The medieval fortress of Castiglione della Pescaia on the Tuscan coast.
The Tuscan coastal town of Castiglione della Pescaia with its medieval fortress – Johannes Gilger, CC BY-SA 2.0, via Wikimedia Commons

As hill towns in Tuscany go, Castiglione della Pescaia offers something for everyone. The town is an ancient fortress that overlooks the Tyrrhenian Sea. Here you’ll find everything: a castle, belltower, port, sixth-century Etruscan walls, pine forests, and sandy beaches. 

Travel Secret: Don’t miss the Diaccia Botrona Natural Reserve, home of the Casa Ximenes and an important spot for migratory birds and thus, for bird watching. Its 14-kilometer trail can be navigated on foot, by bike, or by small boat

8. Volterra

Remaining walls of ancient structure in Volterra.
Volterra, the town of Alabaster, was a powerful Etruscan city – Giorgio Galeotti, CC BY 4.0, via Wikimedia Commons

Known as the Town of Alabaster, Volterra is a historically critical Etrucan town, considered one of the Etrsucans’ 12 dodecapoli or alliance of most important cities. Here, the mineral alabaster has been used since ancient times and was the Etruscans preferred materials for art and pottery. Recently the craft has been revived, and the town even has an Ecomuseum of Alabaster which offers a wonderful mix of craft and history. 

Travel Secret: Make sure to take note of the ancient Etruscan walls of the town. If you’re interested in ancient history, the Guarnacci Etruscan Museum in Volterra needs to be on your list!

Explore More: Etruscan Cities in Tuscany – Ancient Roads to Temples & Tombs

9. Montalcino

Vineyards farm with a breathtaking landscapes in Montalcino
Montalcino is a typical Tuscan hill town

Another important Tuscan hill town in the center of wine country, Montalcino is home to Brunello di Montalcino and Rosso di Montalcino, as well as some of the best wineries in Tuscany. You’ll also find incredible architecture, a historically intact old town, and sweeping landscape views.  

Travel Secret: In July, Montalcino hosts a huge Jazz & Wine Festival that draws international visitors every year. 

10. Monteriggioni 

A sunny day on the street in Monteriggioni with ancient houses
Monteriggioni is a small Tuscan town of just 100 inhabitants located on a hill in Tuscany

This tiny hill town in Tuscany has less than 100 residents! Historically Monteriggioni was a defense hub, which guests can appreciate through a visit to the ancient fortress walls, still standing, and an Armour Museum

Travel Secret: If you’re traveling in the high season, you’ll catch a fun historical tradition: every summer, since medieval times, Monteriggioni hosts a two week long festival. Even Dante Aligheri, the “father of the Italian language” attended the festival here often in his lifetime in the late 1200s and early 1300s!

11. Castellina in Chianti

Aerial view of vineyards and stunning landscapes on Castellina in Chianti
Castellina in Chianti is another Tuscan hill town that is worth visiting

Located, as the name would indicate, in the Chianti wine region, Castellina in Chianti or the little castle in Chianti, is a beautiful hill town in Tuscany. It’s full of ancient buildings, churches, an 11th century fortress, and an archaeological museum. 

Travel Secret: Don’t miss the Via delle Volte medieval tunnel inside of Castellina in Chianti. Originally used, predictably, in defense schemes, during World War II it was used as a bomb shelter, and now it is home to quaint craft shops, osterie restaurants, and small windows with big views. 

12. Poppi

Sunny day in The Poppi Castle in the Tuscan
The Poppi Castle was owned by the aristocratic Guidi family – Photo by Mongolo1984, CC BY-SA 4.0, via Wikimedia Commons

Poppi is a Tuscan hill town located inside of Italy’s Foreste Casentinesi National Park, the National Park of the Casentinesi Forests. The Poppi castle was built by a powerful noble family, and was the site of an important battle in 1289 for which Dante Alighieri was in Poppi, during his exile from Florence. It also offers a quintessential ghost story involving a classic mix: love, murder, and nobility. 

Discover More: 15 Castles in Tuscany – An Enchanting World of Timeless Beauty

Travel Secret: When visiting Poppi, don’t miss the forest for the trees (town)! The National Park of the Casentinesi Forest surrounding the town offers an abundance of trails: for walking, ecological education, hiking, biking, or backpacking. 

13. Capalbio

Houses are surrounded by colorful and beautiful gardens in Capalbio.
A picturesque square in the historic center of Capalbio – Photo by JP-K CC BY-NC 2.0

The hilltop town of Capalbio sits just inland of the Tyrrhenian coastline. One of its more unique attractions is its Tarot Garden, which houses colorful and whimsical statues by artist Niki de Saint Phalle. And don’t forget the castles! Rocca Aldobrandesca is an architectural particularity and has a piano, whereas the Castle of Capalbiaccio offers only ruins following destruction by earthquake. 

Travel Secret: You can walk the whole perimeter of the hill town of Capalbio from atop its defensive wall. This is a great choice for both a stellar view of the landscape and a tour of the town from its edges. 

14. Certaldo

A day view of the medieval town of Certaldo, in Tuscany.
The medieval town of Certaldo, in Tuscany – Davide Papalini, CC BY-SA 3.0, via Wikimedia Commons

This Tuscan hill town is split into two: the old town of Certaldo Alto, and the lower, newer part of town. Certaldo Alto is accessible by car only to residents, visitors can either park outside the walls or take the Certaldo funicular railway that climbs the town’s slope. The town was significant for Italian scholar Giovanni Boccaccio, famous for the Decameron stories – he was likely born in the town and certainly passed away there. Today his home has been made into a cultural museum

Travel Secret: If you’re looking for a quirky stop, Certaldo is home to a Museum of Nails. The museum exhibits a sampling of nails for different purposes and from different times, curated by a carpenter and artisan from Certaldo Alto, Giancarlo Masini.

15. Cortona

A group of tourists sitting on the stairs of Teatro Signorelli in Cortona.
The town of Cortona is a small Tuscan village located on a hill

Cortona is a hill town located in Tuscany’s Val di Chiana. Here you will find a very old Museum of Etruscan Civilization, dating back to the 1700s, as well as the Diocesan Museum from 1945. There is also an Etruscan archaeological park, a fortress, and a unique church called Chiesa di Santa Maria delle Grazie del Calcinaio with a painting known to work miracles. 

Travel Secret: Just 4km outside of Cortona on Strada Provinciale 34 Umbro Cortonese, you can visit the convent Le Celle, which was a hermitage for Francescan monks. With a stream, oak trees, and a terrace, the sounds of nature are prevalent in this retreat. 

Travel Tips for Visiting Tuscan Hill Towns 

A stunning view of landscapes and cloud formations in Tuscan hill towns
The ITS team leaves you some advice for your trip to the Tuscan hill towns

Visiting Tuscany’s hill towns in summer is incredibly popular, but the weather and landscape can be quite dry. While you’ll find lots of other visitors, warm nights, busy beaches, and parties in the summer, the shoulder season is not to be overlooked: the months as summer opens and closes (April to May and September to October). In those periods you’ll find less crowds, more mild weather, colorful landscapes, and even migratory bird watching if that’s of interest to you!

To travel to and between the hill towns of Tuscany, we recommend renting a car. Because of their hilly inclines, there aren’t railways in most of these areas. Some areas are well connected by bus, but many of the roads are not accessible to such big vehicles, and your routes will be both limited and fixes. Renting a car is more certainly your easiest bet to travel through these remote hill towns of Tuscany. The area is also popular for adventuresome hikers and bikers, but some of the roads may be steep and treacherous, so it’s not to be taken as a casual endeavor. 

Why Are Tuscan Towns Built on Hills?

At this point, you might be curious why there are so many towns found on hills in Tuscany. 

This region is very hilly, and being located on the higher points allowed towns to defend themselves better from attack in ancient and medieval times: they could see further, and they were more difficult to reach with weapons. In the past they provided protection from the outside world in wartime, but that sense of escaping from the world below is still preserved in their walled, hilltop ambiance. Visitors often still feel this sense of protection and escape in the towns’ quaint tranquility.