Journey Through Tuscany’s Walled Towns

Four kilometres of tree-lined ramparts embrace the historic centre like a gentle hug, creating an atmosphere suspended between history and legend. Walking or cycling along the walls is a truly unique experience: time seems to slow down, the air is scented with lime trees, and the city’s rooftops reveal themselves from unexpected perspectives. Inside the walls, every alley hides a little surprise — wide squares, Romanesque churches, workshops and cafés that tell the story of Lucca’s everyday life.
By staying at Hotel Ilaria, you can fully breathe in the essence of our magical city. Yet Lucca is not the only town still enclosed by ancient walls: set off to discover Tuscany’s other historic fortified gems.

Just a few kilometres from Siena rises Monteriggioni, one of Tuscany’s most iconic walled villages. Its perfectly circular walls, built in the 13th century, are so striking that they were mentioned by Dante Alighieri in The Divine Comedy: “As in its round of towers Monteriggioni crowns its walls…” — quite an honour indeed!
The fourteen towers punctuating the fortifications, still intact after centuries, offer spectacular views over Chianti and the rolling Sienese countryside. Entering through the ancient gates, you immediately sense the authentic atmosphere of the Middle Ages — among craft workshops, cosy inns and the graceful square dominated by the Church of Santa Maria Assunta.
Today, a panoramic walkway allows visitors to stroll along part of the walls — an experience we highly recommend. The Armoury Museum, meanwhile, takes you on a fascinating journey through medieval life and chivalric history.

Perched on the hills of Arezzo, Cortona overlooks the Val di Chiana with an elegant, timeless silhouette. The walls that protect it date partly back to Etruscan times, in the 5th century BC, and partly to the Middle Ages: walking along the surviving sections means crossing more than two thousand years of history.
Cortona is a maze of sloping lanes, breathtaking viewpoints and lively squares. Within the walls, museums and churches recount a glorious past that stretches from the Etruscan settlements to the brilliance of the Renaissance. Don’t miss the Etruscan Academy Museum, the Basilica of Santa Margherita and the Hermitage of Le Celle — a peaceful retreat founded by Saint Francis.

Ancient and mysterious, Volterra is a place where time seems to stand still. Protected by walls dating back to the 4th century BC, the city still preserves its Etruscan soul, visible in the famous Porta all’Arco, the only surviving gateway of the original fortifications.
During the Middle Ages, the perimeter of the walls was reduced to provide better defence, yet the town retains a powerful, austere charm. Strolling through its narrow streets, you’ll encounter stone towers, alabaster workshops and glimpses opening onto the gentle Tuscan countryside. Visit the Guarnacci Etruscan Museum, one of the oldest in Italy, or Palazzo dei Priori, a proud symbol of Tuscany’s civic power.

Amid the Sienese hills, San Gimignano rises with its towers — the famous case torri — which in the Middle Ages were symbols of wealth and prestige. Of the original seventy-two, fourteen remain, yet they’re enough to create an unmistakable skyline visible for miles around. The walls surrounding the town enclose an extraordinary artistic heritage: frescoed churches, medieval palaces and a lively atmosphere that animates every narrow street. From the top of Torre Grossa, the view opens over the Vernaccia vineyards, home to one of Tuscany’s most renowned wines.
San Gimignano is a place where art and authenticity coexist, and every corner could be a painting.

In the heart of the Maremma, Pitigliano appears like a vision of stone, suspended between sky and rock. Seen from below, the town seems to grow out of the tufa cliffs themselves — a perfect fusion of nature and architecture.
The ancient Etruscan walls mark the beginning of the Vie Cave, a remarkable network of roads carved into the rock that can still be walked today. Within the old town lies a labyrinth of alleys and courtyards, a Jewish Quarter known as “Little Jerusalem”, a 16th-century synagogue and Renaissance palaces telling the story of the Orsini family.

Amid the hills of the Valtiberina, Anghiari is one of the most scenic walled towns in Tuscany. At night, its illuminated walls radiate pure magic; by day, its cobbled streets bustle with workshops and small taverns. In 1440, the famous Battle of Anghiari was fought here, when the Medici defeated the Milanese army — an event later immortalised by Leonardo da Vinci in a mural for Palazzo Vecchio, now lost but forever etched in history.
Walking through Anghiari means breathing in the living past of a village that has preserved its medieval identity — with stone churches, intimate museums and views opening over the valley below. 

From the towers of San Gimignano to the Etruscan stones of Volterra, from the circular bastions of Monteriggioni to the dramatic cliffs of Pitigliano, Tuscany’s walled towns are a perfect harmony of art, history and landscape.
Book your stay at Hotel Ilaria and discover the most timeless side of Tuscany.