12 Beautiful Medieval Cities and Towns in Italy To Step Back in Time

Italy is known worldwide for its historic cities, picturesque coastal towns, and vibrant villages. It’s one of the world’s most beautiful countries, and it’s no surprise that millions of tourists visit it yearly. However, when thinking about Italian history, most people think about the Romans, not realizing Italy also has a rich medieval history.

This medieval history can be seen in the Middle-Age churches, cathedrals, castles, and cobblestone streets that line the nation’s medieval cities and towns. To learn more, here are 12 beautiful medieval cities and towns in Italy you need to visit. We selected these entries because they offer scenic views, medieval architecture, and fascinating medieval landmarks.

Table of Contents

Bologna

The first medieval city on our list is Bologna, the capital of the Emilia-Romagna region in northern Italy. This historic city is famed for its elegant medieval architecture, vibrant culture, and delicious cuisine. If you’re a history buff, you’ll have lots to explore, starting with the medieval city walls.

Mainly built between the 4th and 10th centuries, the Walls of Bologna are adorned with tall stone watchtowers and impressive gates. Once you’ve explored the walls, it’s time to discover the rest of the city’s medieval architecture. Start at Piazza Maggiore, where you’ll find medieval and Renaissance structures, including the Basilica di San Petronio, the Fountain of Neptune, and the City Hall. Don’t miss the Two Towers, either.

Montagnana

One of Italy’s most beautiful medieval towns is Montagnana in Northern Italy. This is a fantastic place to visit if you want to escape the big city and explore somewhere more relaxed. You can expect to find a small town with a big history here. The imposing city walls are the first thing you’ll notice about Montagnana.

These tall stone walls surround the town’s medieval center and feature multiple towers. You’ll come across impressive historical landmarks along the walls, like Vicenza Gate and Rocca degli Alberi. Inside, you’ll find a maze of cobblestone streets begging to be explored. Keep your eyes peeled for the Castle of San Zeno, Mastio di Ezzelino, St. Francis Church, and Piazza Comunale.

Montepulciano

Montepulciano is one of the most famous towns in Italy’s iconic Tuscany region, best known for its world-class wines. Regarding medieval architecture, this picture-perfect destination has much to offer. When not sampling the local red wine, get lost among the charming streets lined with traditional Italian stone houses and breathtaking monuments.

Fortezza Montepulciano is the crowning glory of the town, also known as the Fortress of Montepulciano. This military fortress was constructed during the 13th century and is home to lush gardens, tall medieval walls, watchtowers, and various significant buildings, including the Consorzio Del Vino Nobile Di Montepulciano. Montepulciano’s points of interest at the fortress include the Palazzo del Capitano del Popolo, Cathedral Saint Mary Of The Assumption, and Porta delle Farine.

Civita di Bagnoregio

If you’re searching for a fairy-tale medieval destination in Italy, look no further than Civita di Bagnoregio. This picturesque hilltop village was founded in the 7th century in Central Italy, north of Rome. Its beautiful narrow streets are lined with medieval buildings that have stood the test of time.

A long bridge leads to the top of the hill, which sits precariously on what looks like a large rock. We highly recommend taking photographs from the bridge, as the views of the town and surrounding mountain landscape are spectacular. Inside Civita di Bagnoregio, wander the streets, searching for the most exciting landmarks. You don’t want to miss the Church of St. Nicola, Giardino del Poeta, Museo Antica Civitas, and Piazza San Donato.

Orvieto

Orvieto is a small city perched on a volcanic bluff in Umbria, Central Italy. Umbria is renowned for its stunning natural scenery and medieval hilltop towns, and Orvieto is a fine example of what the region has to offer. Surrounded by lush forests, the scenic views from atop the hill will always be exciting.

As for the city, we don’t know where to start. You’ll be blown away at every corner by beautiful buildings and landmarks. However, the 13th-century Duomo di Orvieto is arguably the most impressive sight in the city. It features a gorgeous mosaic facade and is home to a marble Pietà sculpture. Other noteworthy attractions include the National Archaeological Museum of Orvieto, Pozo de San Patricio, and Torre del Moro Orvieto.

Positano

You’ll likely know Positano best as a famous tourist destination along the Amalfi Coast. Millions of tourists visit the town yearly to soak up the sun on the pebbled beachfront, sip Aperol Spritz on a balcony, and admire the town’s famous pastel-colored houses. However, during the Middle Ages, things were very different.

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In medieval times, this iconic hilltop town was a significant trading port. Spices, silk, and other goods would be traded with the Middle East. The town’s success led to the construction of many beautiful buildings, including the 13th-century Chiesa di Santa Maria Assunta. The best way to explore the town is to get lost meandering through the steep, narrow streets. You could stop for a refreshing beverage on your way.

Siena

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Siena might not be one of Italy’s most popular cities, but it’s undoubtedly one of the most interesting. The city’s medieval red brick architecture, lively Middle Age squares, domineering cathedral, and dense forest surroundings are an Instagrammer’s paradise. Of course, history lovers also fall head over heels in love with the city.

This walled city’s main attraction is Duomo di Siena, a 13th-century Gothic cathedral featuring vibrant murals, an intricately crafted facade, and tall towers. You also don’t want to miss Piazza del Campo, a lively square dominated by the remarkable 13th-century Palazzo Pubblico. At the square, you’ll also find the Gothic Town Hall, Museum of Torture Siena, and Loggia della Mercanzia.

San Gimignano

One of the main reasons we love San Gimignano, a hilltop town in Tuscany, is because it’s often referred to as the “Manhattan of the Middle Ages,” and we find that hilarious. Declared a UNESCO World Heritage Site in 1990, the town is given this nickname because it features several majestic medieval towers resembling an ancient version of the Manhattan skyline.

Best known for its architecture, the city offers a well-preserved historic center jam-packed with exciting sights. Conveniently, the two main streets, Via San Matteo and Via San Giovanni meet at Piazza del Duomo, where you’ll find Duomo di Santa Maria Assunta. This allows tourists to explore the town’s main areas easily. Other points of interest include Palazzo Vecchio del Podestà, Torre Grossa, and Piazza della Cisterna.

Lucca

Situated in the Tuscany region, Lucca is easily one of Italy’s most interesting and beautiful cities. It sits on the Serchio River, surrounded by lush countryside, and is renowned for its well-preserved medieval and Renaissance architecture. Lucca’s Renaissance-era walls still stand proudly today, lined with trees and serving as a local hiking and cycling trail.

Meanwhile, the historic center and its cobblestone streets are lined with vibrant buildings and monuments. You don’t want to miss Plaza del Anfiteatro, the Aqueduct of Nottolini, the Guinigi Tower, and the Cathedral of Lucca. As you explore, you’ll also come across many quaint boutiques, high-end restaurants, and charming cafes.

Civitella del Tronto

With beautiful natural surroundings, a lovely hilltop fortress, quaint narrow streets lined with medieval and Renaissance architecture, and various fascinating stories to tell, Civitella del Tronto is a traveler’s dream. When you’re not admiring the epic countryside views, you’ll find yourself discovering local wonders.

The history of this town in the Abruzzo region is interesting. In the past, it has been besieged, invaded, and subject to war. With that in mind, it’s no surprise that a large fortress dominates the town. From the fortress, you can enjoy panoramic views of the medieval town below and visit numerous attractions like La via più stretta. Don’t forget to visit Santuario di Santa Maria dei Lumi in the town, either.

Verona

Well-known for being the home of Shakespeare’s Romeo and Juliet, Verona, otherwise referred to as the “City of Love,” is a fascinating city exploding with medieval and Renaissance architecture. The city’s multitude of historical landmarks have made the city of Verona a UNESCO World Heritage Site.

The historic center, Centro Storico, features many popular attractions, including Piazza delle Erbe, Verona Arena, and Juliet’s House, or at least the building believed to have inspired Shakespeare’s play. In Piazza delle Erbe, you’ll find a local market that’s been in operation since the Middle Ages. You can buy souvenirs, flowers, and farm produce here. Other notable attractions in Verona include the Torre dei Lamberti, Castelvecchio Museum, and Scaliger Tombs.

Massa Marittima

Massa Marittima is the final Italian medieval town on this list. It’s a storybook destination that wouldn’t look out of place in a Disney movie. This breathtaking medieval town sits atop a hill overlooking Italy’s picturesque countryside. However, it’s most loved for its impressive 13th-century walls and beautiful medieval buildings.

In the heart of the town lies its historic center. You’ll find many interesting buildings and attractions here, including Piazza Garibaldi. This cobblestone square features castle-like facades, pastel-colored buildings, and elegant churches. The 13th-century Massa Marittima Cathedral is only a short walk from the square. Other popular attractions in Massa Marittima include the Torre del Candeliere, the Museum of Sacred Art, and the Museo della Miniera.