From the hilltop vistas of Tuscany to the spiritual serenity of Umbria, these towns offer a glimpse into a bygone era, each with its own unique charm and character. Whether you’re wandering through the cobbled streets of Volterra, soaking in the spiritual ambiance of Assisi, marveling at the mosaics in Ravenna you’ll find that each destination tells a story of its rich heritage. Join us as we dive into the captivating allure of these medieval gems, perfect for history enthusiasts and travelers alike.
1. Volterra, Tuscany
Perched on a hilltop in Tuscany, Volterra is a captivating medieval town known for its Etruscan heritage and stunning alabaster craftsmanship. The ancient walls and narrow cobblestone streets lead visitors to historical sites like the Roman theater and the impressive Piazza dei Priori, where the town’s rich past comes to life amidst breathtaking views of the surrounding countryside.
2. Assisi
A UNESCO World Heritage site, Assisi is renowned as the birthplace of St. Francis and exudes a serene spiritual atmosphere. The town is characterized by its charming stone buildings, winding streets, and the majestic Basilica of San Francesco, adorned with exquisite frescoes that attract pilgrims and tourists alike, all set against the backdrop of the picturesque Umbrian hills.
3. 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. Visit the historic Old Town and its charming piazzas. Here, you’ll find well-preserved cobblestone streets, family-run restaurants, and open-air markets. Climb the city’s tallest tower, Torre Grossa, standing at 177 feet, for panoramic views of San Gimignano and the Tuscan countryside.
4. Ravenna
Famous for its stunning Byzantine mosaics, Ravenna boasts a rich tapestry of history that dates back to ancient Rome. Visitors can explore its eight UNESCO World Heritage sites, including the Basilica di San Vitale and the Mausoleum of Galla Placidia, while wandering through the town’s charming streets filled with cafes and shops that reflect its artistic heritage.
5. 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, and the bridge is one of the highlights of visiting Civita di Bagnoregio.
6. Montalcino
Nestled in the heart of Tuscany, Montalcino is celebrated for its world-renowned Brunello wine and breathtaking landscapes. The medieval town features a striking fortress and picturesque streets lined with wine cellars, offering visitors the chance to indulge in wine tastings while soaking in the stunning views of the surrounding vineyards and rolling hills.
7. 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 architecture, grab a bite, or meander through the arched colonnades.
8. 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. Verona is a UNESCO World Heritage Site. The historic center, Centro Storico, is home to major attractions. You’ll find Juliet’s House, the Verona Arena, and the Piazza delle Erbe, which hosts an outdoor market that’s been thriving since the Middle Ages.
9. 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. At Piazza del Campo, you’ll find the towering Torre del Mangia overlooking the city.
10. 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.
11. Roccantica, Rieti
Roccantica is a charming hilltop village just a 75-minute drive from Rome. This old Italian town boasts a labyrinth of staircases made with greystones and cobbles preserved over thousands of years. After getting lost around town, visit Roccantica’s famous Gothic churches, San Valentin and Santa Caterina, to admire the perfectly-preserved medieval architecture. Inside Santa Caterina, you’ll find a range of 14th-century frescoes that will leave you in awe.
12. Ferrara, Emilia-Romagna
Ferrara is one of the most important Renaissance cities in Italy. 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. Ferrara is most famous for “Cappellacci di Zucca”, a pasta with a unique hat shape. Stop by the town’s oldest wine bar and restaurant, Al Brindisi, for a taste of traditional Ferrara cuisine and wine.
13. Perugia, Umbria
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.
14. 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.
15. 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. Pitigliano hosts a handful of medieval and Jewish landmarks. Some notable points of interest include the Fontana delle Sette Cannelle, the Museum of Palazzo Orsini with its beautiful frescoes, and the Church of Santa María.
16. 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.