Italy is full of medieval towns that seem frozen in time, with cobbled streets, stone towers, and hilltop views straight out of a movie. These places offer more than just history—they’re packed with character, local traditions, and landscapes that make you want to stay awhile. If you’re drawn to old-world charm and slower-paced travel, here are 12 beautiful medieval towns in Italy worth adding to your list.
San Gimignano, Tuscany
Internationally renowned as the “Medieval Manhattan”, San Gimignano is a stunning hilltop town in Tuscany, southwest of Florence. At its prime, this medieval city had 65 towers dominating its skyline. The grandeur and magnificence of these towers show the ambition and mastery of medieval architects and the city’s ability to defend itself against enemy attacks. While many of the towers were destroyed during wars, the ones you see today are a popular tourist attraction.
Civita di Bagnoregio, Viterbo
Civita di Bagnoregio is a hilltop medieval village in Viterbo, 80 miles from Rome. The scenery of this town is surreal. This village sits on a limestone cliff and is only accessible via a suspended footbridge known as the Porta Santa Maria gateway. The 400-yard pedestrian bridge spans over the Calanchy Valley, making it impossible for an invasion. Today, the bridge is one of the highlights of visiting Civita di Bagnoregio. Visitors love taking photos here.
Montalcino
Montalcino is a stunning town located in the Tuscan region of Italy, renowned for its world-famous Brunello di Montalcino wine and diverse natural beauty. Nestled among rolling hills, this picturesque town offers visitors a unique opportunity to immerse themselves in traditional Italian culture while exploring its charming cobblestone streets and fascinating historical sites.
Bologna, Emilia-Romagna
Bologna is a vibrant, medieval city and the capital of the Emilia-Romagna region. This lively city is known for its elegant medieval architecture, sun-drenched Adriatic beaches, and delicious food. If you’re a food connoisseur, you’ll find lots of foodie activities in Bologna, from visiting a cheese factory to making your own pasta. If you’re a history lover, you will also have lots to explore. Piazza Maggiore is an excellent place to admire Renaissance architecture, grab a bite at a café, or meander through the numerous arched colonnades.
Verona, Veneto
Verona is known as Italy’s “city of love” thanks to its role as the setting for Shakespeare’s “Romeo and Juliet”. This gorgeous medieval city boasts stunning architecture, from churches and cathedrals to castles and piazzas. During the Della Scala family’s rule between the 13th and 14th centuries, Verona saw exponential growth in wealth and prosperity. Today, the city hosts several of the most famous landmarks in Italy.
Siena, Tuscany
Siena is one of the best cities in Italy you’ll ever visit. The city’s medieval red brick buildings, its fan-shaped Piazza del Campo, and the Gothic Duomo di Siena are a few attractions that make this city a must-visit destination. This walled city in Italy is located right in the center of Tuscany and hence attracts lots of wine lovers and history buffs alike. The Duomo di Siena boasts an impressive interior with mosaic marble floors and ornate frescoes. You’ll also find the finest collections of artwork by Donatello and Michelangelo.
Stilo, Reggio Calabria
Stilo is one of the most stunning small villages in Italy. Standing about 1,312 feet above sea level, this quaint town is surrounded by lush forest and looks out to fantastic views of the Ionian coast. This ancient medieval town is most famous for its remarkable Byzantine cathedral Cattolica di Stilo, dating back to the 9th and 10th centuries. The building’s unique design features domes, arches, and red bricks that continue to overlook the valley below after centuries.
Ferrara, Emilia-Romagna
Ferrara is one of the most important Renaissance cities in Italy. This city was once the hub of culture, art, politics, and cuisine in Europe during the Middle Ages. Ferrara was ruled by a prominent dynasty, the House of Este, which made significant contributions to the Renaissance-style architecture you see today. You can visit the Este Castle for a sneak peek into the power and greatness of this family.
Perugia, Umbria
If you’re a music and chocolate lover, there’s no better city in Italy for you to visit than Perugia. Characterized by defensive walls, medieval architecture, and stone arches, Perugia is one of the best places to visit in central Italy. Apart from its famous chocolatiers and jazz festivals, Perugia has plenty of things to admire. At the Palacio de los Priores, you’ll find impressive local art from the 13th century. The palace is located in Piazza IV Novembre, where you’ll see Gothic cathedral structures, Renaissance murals, and frescoes.
Erice, Sicily
Erice is one of the most magnificent cities in Southern Italy. This hilltop town boasts incredible historic medieval churches, castles, and cathedrals. But the most famous attraction in Erice would have to be the two castles. At Pepoli Castle, you’ll find an interesting collection of stones, ceramics, and bronze relics. Meanwhile, Venus Castle sits atop the highest point on Mount Erice, giving you scenic views of the village and its dazzling beaches.
Pitigliano, Grosseto
Nicknamed “Little Jerusalem”, Pitigliano is one of the most beautiful Italian towns in Tuscany. Carved from volcanic rock, this medieval city boasts the most impressive show of historical and Renaissance architecture in Italy. The town got its nickname for being a safe haven for Jewish refugees fleeing from Rome. Today, Pitigliano hosts a handful of medieval and Jewish landmarks.
Positano, Salerno
Positano is a colorful, cliffside village sitting along Italy’s Amalfi Coast. This gorgeous town is a renowned tourist attraction thanks to its pebblestone beaches, narrow streets, and charming clifftop cafes. But Positano has been one of the most important towns in Southern Italy for many years. The village was a wealthy trade port for the Amalfi Coast during the Middle Ages, trading spices, silk, and other precious goods with the Middle East.
Laura Lynch, creator and writer of Savored Journeys, is an avid world traveler, certified wine expert, and international food specialist. She has written about travel and food for over 20 years and has visited over 75 countries. Her work has been published in numerous guidebooks, websites, and magazines.