Written by Elizabeth Heath
Elizabeth Heath is a travel and lifestyle writer and editor who has been tromping through the woods and fields of Umbria for the past 13 years. Her work appears in The Washington Post, Travel + Leisure, Smithsonian, and many other outlets. You can follow her on Instagram here.
Atmospheric and romantic, Tuscany’s hill towns offer visitors a journey back in time. If you’ve ever taken a train or driven through Tuscany, you’ve likely spotted them from a distance—stone-built hill towns that loom over the surrounding countryside of vineyards, olive groves and sunflower fields. Most are as beautiful and intriguing up close as they are from afar, and they often hide significant artistic, architectural and archaeological treasures.
But those hill towns weren’t constructed for their aesthetics. After the definitive fall of the Roman Empire and the security it provided, rural inhabitants of the Italian peninsula increasingly found safety in numbers. They banded together in towns on the tops of hills, often built on the site of former Etruscan settlements or Roman villas. During roughly the 10th to 12th centuries, in the absence of a central government, regional lords seized many of these settlements and built castles around them—offering protection from marauding hordes in exchange for the fealty of the vassal peasants. Today, these monuments to a violent, dangerous period in Italian history are for many visitors the archetypal image of Tuscany.
We’ve included a few better-known choices in our brief guide to Tuscany’s hill towns below, as well as some of the most beautiful towns in Tuscany you may be less familiar with. So what are you waiting for? Tuscany is calling.
SAN GIMIGNANO
San Gimignano. Photo credit: Shutterstock
On a tour of the Tuscan countryside, a stop at this quintessential hill town is almost obligatory. Known as “the Manhattan of the Middle Ages,” the San Gimignano skyline was once filled with 72 tall, skinny medieval towers. Today, only 14 remain, but they continue to make for an “ahh”-inspiring first impression. And if you’re feeling energetic, a climb to the top of 54-meter high Torre Grossa, the tallest of the towers, rewards with gorgeous views of the cityscape and countryside. Elsewhere inside the well-preserved centro, you’ll find broad piazzas, a handful of museums, a magnificently frescoed cathedral, and several homey restaurants serving authentic regional fare.
MONTEPULCIANO
Montepulciano. Photo credit: Shutterstock
Hardly unknown but still less visited than some of its bigger neighbors, Montepulciano sits in southeast Tuscany, not far from the border with Umbria. The abundance of Etruscan and Roman archaeological finds in and near the town demonstrates its long history and importance as a strategic crossroads. For the centuries of the late Medieval and Renaissance, Montepulciano was a prize of both Florence and Siena. Today, its Renaissance-era piazzas and palazzos and its rustic wine cellars are coveted by visitors eager to sample Vino Nobile di Montepulciano, variations of which have been produced in these verdant hills since at least the 8th century.
Montalcino
Montalcino. Photo credit: Shutterstock
The Tuscan wine boom of the 1970s and 80s was centered around Montalcino and its famous Brunello. But this highly coveted wine isn’t the only reason to visit this walled city, which sits high on a hill overlooking the surrounding Val d'Orcia. Inside the walls unfolds a warren of narrow streets lined with authentic family-run shops and eateries and, of course, enoteche (the plural of enoteca) wine shops are everywhere, offering tempting samples or souvenirs. An imposing 14th-century fortress is worth visiting, in part for its sweeping views of the rolling hills and valley around it. Montalcino is a place to wander, dine on local specialties, taste some of Italy’s best wine, and get lost in this small piece of Middle Ages authenticity.
BARGA
Barga. Photo credit: Shutterstock
There are Tuscan hill towns that emerge from undulating fields, and then there are hill towns. Barga, in northern Tuscany, is nestled among similarly sized hills, with the peaks of the Apulian Alps emerging to its north. Since at least the 800s, Barga was an important stopover for merchants and pilgrims coming down from the mountains. Today, its remote location and the dramatic terrain surrounding it give it a real sense of rustic coziness. Modern visitors are often adventure-seekers who use Barga as a base for spelunking, mountainbiking, canyoning, and other active sports.
PITIGLIANO
Pitigliano. Photo credit: Shutterstock
A sharp switchback turn on the provincial road through Maremma reveals one of Tuscany’s most astonishing hill towns, Pitigliano, which sits on a volcanic tufa plateau high above the wild terrain around it. Pitigliano’s roots date to the Etruscan era when it was connected to nearby settlements via the fascinating Vie Cave (cave roads)—hidden passageways carved through the sheer rock face in the valley below. Pitigiliano’s centro storico feels wonderfully ancient, especially in La Piccola Gerusalemme—the “Little Jerusalem”, one of Tuscany’s oldest Jewish quarters, first established when Jews fled persecution in Rome to settle here.
PIENZA
Pienza. Photo credit: Shutterstock
Among a cluster of delightful hill towns in the Val d’Orcia, Pienza is the only one that’s a UNESCO World Heritage City—not for its medieval roots but for its Renaissance ones. Though the city dates to at least the 9th century, the Pienza we see today was formed in the mid-1400s, when Pope Pius II, who was born into the Piccolomini family of Pienza, took an interest in revitalizing his place of origin. Today, the Piccolomini Palace, the Bishop’s Palace and the Duomo form part of Pienza’s well-preserved heart, which is considered a perfect example of Renaissance elegance and symmetry.
VOLTERRA
Volterra. Photo credit: Shutterstock
The past feels very close indeed in Volterra, which has been continuously inhabited since the 8th century BCE, when it was one of the dodecapoli—the alliance of 12 cities now known as the Estrucan League. Volterra’s heart is very much medieval, with many buildings dating to the 1200s, and it’s rife with ancient sites, such as an Estrucan acropolis and a Roman theatre. Parts of the 3rd-4th century BCE Etruscan walls still exist, incorporated into later medieval fortifications. Fans of the Twilight films will associate Volterra as the home base of the sinister Volturi clan, but those scenes were actually filmed in Montepulciano.
This is just a sampling of some of Tuscany’s many beautiful hill towns. The best way to find your favorite? When you see one of those small towns appear on the next hill, make it a point to stop and explore—chances are you won’t be disappointed.
