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Tuscany is always high up on the Italy travel itinerary with incredible cities such as Florence, Pisa and Siena, with an undulating landscape. And while the cities are reason enough to visit Tuscany, they leave one of the regions’ other major assets overlooked — its authentic old-world towns and villages.
Often built on hilltops as vantage points for land control and power, spanning from the ancient Etruscan era to the 13th century Battle of Montaperti (Florence-Siena war), Tuscany’s towns and villages are where you’ll find the region’s best kept historical secrets, as well as its best viewpoints and local charm. In this article, we span Tuscany high and low, from the mountains to the sea, to bring you its best authentic towns and villages.
San Gimignano
San Gimignano, overlooking the rolling Siena hills, has perhaps one of the most impressive skylines in all of Tuscany, as around a dozen stone-built square towers rise above the town beckoning travelers from afar.
In the 13th century however, there would have been over 70 towers filling the sky, as the wealthy residents who built them competed for superiority.
Today the ‘Town of Fine Towers’’ Historic Centre has become a UNESCO World Heritage Site, heralded for its mix of Romanesque and gothic architecture, which can be particularly appreciated in the Piazza Duomo and Piazza della Cisterna where you can sit, relax, and soak up the worldly charm.
Volterra
Sitting nobly upon yet another of Tuscany’s hilltops, Volterra is a particularly historic town surrounded by ancient stone walls dating back to the 4th century BC, which you can walk along to see the scenic Era Valley and a recently discovered Roman amphitheater.
The walls encase a wealth of intriguing architecture, from the medieval Volterra Cathedral to Romanesque palaces, and the Acropolis which guards secret ancient tombs.
Aside from being known as a target of a tug of war between Florence and Siena in the 1200’s, Volterra is also known for its artisanal excellence in producing stark white alabaster carvings, which make a memorable souvenir.
Pienza
Reigning over the golden fields of the Orcia Valley, one of UNESCO’S World Cultural Landscapes, Pienza enthralls with its simplistic and clean ‘urban Renaissance’ architecture dreamed up by Pope Pius II who wanted to create a utopia.
Making it his summer residence, Pienza became filled with palaces, three of which are found in Piazza Pio II, the only remaining historic center in Italy still completely intact. You’re bound to discover other historical gems as you take a romantic stroll through Pienza’s steep cobbled streets, which are aptly named ‘Kiss Street’ and ‘Love Street’.
Pienza has also gained prominence through its tie to the famous Italian pecorino cheese, celebrated with its own festival every September.
Lucca
With the Apuan Mountains to the east, the Tuscan coast to the west, and Pisa to the south Lucca is the ideal place from which to explore the best of Tuscany. As one of the few towns not to be built on a hill, Lucca is more sprawled out and boasts plenty of green spaces around its ramparts, including the Lucca Botanical Garden, giving it a splendidly relaxed vibe.
Known as the ‘city of 101 churches’, Lucca also has a wealth of fascinating historical religious buildings ranging from medieval to Roman to Renaissance, but if you only visit one, make it St. Martin’s Cathedral which is filled with art and wonder.
Barga
With nothing but chiseled mountains carpeted in luscious greenery rising from every angle, Barga is one of the most visually stunning towns in Tuscany. And of course, among this scenic landscape you’ll find a web of breathtaking hiking trails, but if you’d rather appreciate its beauty from the comfort of Barga, head to the ramparts surrounding the impressive Romanesque Collegiate Church of San Cristoforo at the top of town.
Barga is also a cultural hub of Tuscany, as not only does it hold annual opera and jazz festivals, it’s long been home to a number of artists and writers, including famous poet Giovanni Pascoli.
Cortona
Stacked haphazardly on a hillside looking out onto the heart of Italy, Cortona appears at first sight to be a modest fortified medieval town.
Narrow cobbled streets lined with pale stone houses wind steeply onto a buzzing piazza enclosed by centuries-old palaces and local shops selling everything from groceries to local art. But beyond the usual fancies of such a town is the history that has formed it, and Cortona’s history as an Etruscan epicenter is what makes it a must-visit.
The Etruscan Museum (MAEC) holds myriad artifacts excavated and preserved from Etruscan times, and an Archeological Park where ancient city fortifications and even a Roman road have been discovered.
Monteriggioni
Monteriggioni is situated just a few miles north of Siena, and although it’s one of the smallest villages in Tuscany, it holds a special place in Italy’s history as a stronghold in the Siena-Florence war.
Like most medieval towns, Monteriggioni is surrounded by an intimidatingly tall wall (which makes for a wonderful village viewpoint) with bulky watchtowers protruding from it every few meters, but unlike most, its wall is distinctively circular, making it a particularly intriguing site to see.
The town itself, accessed only through a gate, is also full of intriguing historical sites, as well as a great number of charming little Italian restaurants and shops.
Pitigliano
Built upon a large rocky outcrop protruding vividly from the surrounding green hills, Pitigliano quite literally stands out from any other Tuscan village, as its rising volcanic rock face blends into the town ramparts, which then seemingly merge into tumbling stacks of old four-story houses all made from the same rock they were built on.
Many refer to Pitigliano as ‘Little Jerusalem’, partly because of the physical similarities to the ancient city, but also because of its historically prominent Jewish presence.
However, this village’s history is evidenced to go as far back as the bronze age, so you’ll find everything from necropolis ruins, to an ancient cave system, to the Medici aqueduct and even 7th century BC Etruscan walls.
Collodi
Despite being a very small village cascading like a thin stream from the medieval Rocca Antiqua castle on the hilltop to the impressive Villa Garzoni at the foothill, Collodi has gained prominence in Tuscany’s landscape. Why? This seemingly insignificant town is the birthplace of one of Italy’s most significant authors, Carlo Collodi, who wrote the world-famous Adventures of Pinocchio.
Today, the legend of Pinocchio lives through a whimsical theme park and garden dedicated to his adventures, and it’s enjoyed by everyone young and old. However, Villa Garzoni’s landscaped garden has a stylish edge over Pinocchio’s, and is like a botanical paradise amongst the rugged Tuscan landscape that surrounds it.
Fosdinovo
Fosdinovo sits tall and mighty on a hilltop edging the beautiful Tuscan-Emilian National Park, offering breathtaking vistas of verdant mountains which surrender to the throes of the azure Atlantic, as well as beautiful nature trails.
The best place from which to enjoy these views is from the 11th century Malaspina Castle-turned-palace, which speaks to its tumultuous history of battle with its tall ramparts, trap doors, and torture room, and to its noble residents and guests (including Dante) with a great hall adorned with frescoes, a throne room, and a grand marble entrance.
The village streets themselves are also filled with old-world Italian charm, where a medieval festival is held every July.
Montepulciano
With vineyard-filled hills of the Orcia Valley rolling from each angle of this high hilltop town, Montepulciano offers one of the best typically Tuscan views in the region.
Its steep hills and access to a lot of wine barrels means that Montepulciano is the ideal place for a good old barrel race, which has a dedicated festival every year.
The town also looks out over the must-see iconic domed Renaissance Church of San Biagio, but there are plenty of churches, palaces and other impressive historical buildings to be found within its center too. In the cobbled Piazza Grande you’ll find the impressive Palazzo Comunale and Montepulciano Cathedral.
Arezzo
Arezzo may be a little one of the larger and busier towns and villages, but this ancient Etruscan city (as it was thought of back then) should not be missed off your Tuscan itinerary, especially if you’re wowed by Italy’s unique historical architecture.
The town is filled with churches, monuments, palaces, fortresses, and even a Roman amphitheater, brimming with some of the finest examples of Italian art and culture. Piazza Grande, the town’s main square adorned with many colorful coats of arms and filled with delightful restaurants, is a great place to start your discovery.
Be sure to check out San Francesco Basilica with the world-renowned fresco ‘Legends of the True Cross’ and the mesmerizing Medici Fortress.
About the Author: Emily Draper
Originally from the UK, Emily Draper has lived in Chile, with an Amazonian tribe in Peru, in a Wisconsin trailer park, and on a boat in the Mediterranean Sea. Considering herself, and the rest of us, as global citizens, Emily’s mission as a writer and journalist is to expand global consciousness of the fundamental importance of travel, culture, and diversity.