Step Back in Time: 15 Enchanting Medieval Cities You Can Explore Today
Have you ever wanted to walk on land where Knights once roamed and where Kings held court? Even without a trip to an amusement park rollercoaster, medieval cities will take you back through the pages of time with their cobblestone streets, stone walls, and centuries-old architecture.
The 3-kilometer fortified walls of Carcassonne and the 1,940-meter city defenses in Dubrovnik are legacies of a bygone age and attract millions of visitors yearly. These are more than just pretty visuals; they are journeys into a world where empires both arose and fell.
Assuring a spellbinding journey in time, they offer unique attractions and travel tips to help you plan your exploration. Ready to time travel? Many of these are enchanting destinations.
Carcassonne, France

If you are looking for a medieval masterpiece, Carcassonne is it. This UNESCO World Heritage Site is a fairytale, surrounded by double walls and 52 watchtowers. Walk the colorful medieval streets, and don’t miss the Château Comtal (a 12th-century castle with stunning views).
Be in the middle of the citadel for an entirely consequential experience. Local specialties such as cassoulet (slow-cooked stew) are must-tries.
Rothenburg ob der Tauber, Germany

It’s the kind of city that could have been designed just for its postcards. Its impeccably preserved streets and half-timbered houses still attract photographers and dreamers from all over the world.
Walk around the ancient old town walls and peek at the Christmas Museum, which is open all year. Visit in December to get the magical Christmas market. Many hotels also offer medieval-themed stays!
Dubrovnik, Croatia

A city of medieval architecture and coastal beauty, Dubrovnik is famous for being King’s Landing in Game of Thrones. A series of formidable walls, which primarily date from the 12th to 17th centuries, run about 1,940 meters (6,365 feet) and stand up to 25 meters (83 feet) in height.
Amongst the finest in the world, these fortifications provide panoramic views of the Adriatic Sea.
The off-peak seasons (spring and autumn) are the best times to visit, owing to fewer crowds and better weather conditions.
San Gimignano, Italy

San Gimignano, often called the “Town of Fine Towers,” is renowned for its medieval architecture. In the 14th century, wealthy families erected 72 tower houses as symbols of status and power.
Today, fourteen towers survive and still form the town’s skyline. In addition to its historic towers, quaint squares, and local wine, you can rent a Vespa for an unforgettable ride through the surrounding Tuscan countryside.
Bruges, Belgium

Often referred to as the “Venice of the North,” Bruges enchants with its canals, cobblestone streets, and iconic medieval belfry.
Begin your day with a boat tour and finish it off at De Halve Maan Brewery. Indulge in traditional waffles from street vendors, which are as heavenly as they sound.
Tallinn, Estonia

Tallinn’s Old Town, a UNESCO World Heritage Site since 1997, is celebrated as one of Europe’s best-preserved medieval cities. The Alexander Nevsky Cathedral, completed in 1900, sits atop Toompea Hill when Estonia was under the Russian Empire.
Renowned for its striking architecture, this Orthodox cathedral holds 11 bells, the biggest weighing 15 tons, making it the largest bell in Tallinn. Visiting these landmarks lets you gain deep insight into Tallinn’s historical and cultural mélange, where historical heritage and modern vibrancy meet. Visit Christmas markets in the winter for an even more fantastic experience.
Siena, Italy

Piazza del Campo in Siena is famous for its distinctive shell shape, with a circumference of nearly 333 meters. Divided into nine sections, symbolizing the Noveschi, the medieval rulers of Siena, its red brick pavement is laid. Since 1701, this square has been the site of the Palio di Siena, a historic horse race.
Twice a year, it is held on July 2 and August 16. Ten of Siena’s seventeen contrade (districts) participate in a three-tracking lap face fling around the piazza. Each race takes approximately 90 seconds and takes all horses and riders to navigate the challenging course amidst enthusiastic crowds.
Siena still clings to its traditions, attracting thousands of spectators to its event. Finally, climb the Torre del Mangia to get the best view of the city and the surrounding countryside.
Toledo, Spain

Toledo represents architectural and cultural diversity, where Christianity, Judaism, and Islam harmonize wonderfully. The Alcázar of Toledo is a monument to medieval Spanish power and a Roman-era fortress that dominates the city’s skyline.
In the reigns of Alfonso VI and Alfonso X, considerable reconstructions took place, and in 1535, under Charles V, a notable restoration took place. The Alcázar has served various roles throughout history, including as a royal palace and military academy. Visit local artisans to witness the making of Damascene jewelry and swords, a craft Toledo is famous for.
Edinburgh, Scotland

Picture this: centuries-old streets weaving through a history-steeped city, a towering fortress crafted on volcanic rock. The medieval Old Town makes up Edinburgh’s upper half and lures you to Edinburgh Castle to learn more about its past.
The castle, a symbol of Scotland’s power, draws over 2 million visitors annually, making it one of the country’s most popular attractions.
Head down for the Edinburgh Festival Fringe in August, the world’s most extensive and eclectic arts festival. There’s no better way to experience the past and present than visiting Edinburgh.
Prague, Czech Republic

Imagine walking around in a city whose every street has a magical fairy tale quality. Prague, the “City of a Hundred Spires,” keeps its gothic charm alive with stunning landmarks like the iconic Charles Bridge and the Astronomical Clock in Old Town Square, captivating visitors for over 600 years.
The clock, one of the oldest of its kind, attracts more than 2 million visitors each year. Take a walking tour of these iconic sights without the crowds. Prague is a city full of giant spires, beautiful bridges, and medieval squares; each corner is stained with a story, and the story is a captivating display of past and present.
York, England

As with its Roman and Viking history, York mixes medieval charm with Roman and Viking history. One of the largest Gothic cathedrals in Europe, the magnificent York Minster is among the world’s most significant buildings.
A narrow, winding shopping street framed by overhanging Tudor buildings, the Shambles is also an excellent place for a walk and shouldn’t be missed. Time your visit to the York Mystery Plays, a tradition dating back to the 14th century.
Rhodes Old Town, Greece

What if a city is a place of almost paradise and history mixed? For the history–lover’s dream, Rhodes encircles 4 km of old medieval walls, still standing. In this fortified city stands the spectacular Palace of the Grand Master, the former residence of the Knights of St John, and the lovely Street of the Knights, where time has stopped.
Attracting over 1.5 million visitors a year, Rhodes’s clear blue Aegean waters and historical wonders draw in tourists. It is packed full of history and belongs on your travel bucket list.
Bratislava, Slovakia

A medieval gem, Bratislava’s Old Town nestles along the banks of the Danube River. Between colorful facades and cobbled streets through centuries, the history lies. Passing through its squares, you’ll be charmed by this fruitful European surprise.
Bratislava Castle stands proudly on a hill, with views of the city and beyond, and more than 1.5 million visitors yearly for its vistas. If you ever want a taste of Slovak culture, savor a glass of Slovak wine in one of the cozy taverns that pepper the tiny heart of the city. Once in Bratislava, there’s plenty of history, stunning views, and even local flavors.
Avila, Spain

Ávila, often called the “City of Stones and Saints,” is renowned for its remarkably well-preserved medieval walls. Built mainly during the 11th and 14th centuries, these fortifications enclose the historic city center, forming a perimeter of some 2,516 m.
The City of Ávila, with its old town, including its Walls, extramural churches, etc., was identified as a UNESCO World Heritage Site in 1985 due to its historical significance and exceptional preservation.
This designation also attests to Ávila as an excellent example of a fortified medieval city. Walking along the walls can have unique views of the city’s medieval layout and surrounding landscape.
Colmar, France

Colmar is effortlessly charming and endearingly quaint with its medieval half-timbered houses, ornate canals, and flower-fringed streets. It’s also part of the Alsace wine region, so anyone who fancies a good wine can look forward to finding one. For postcard-worthy views, take a boat ride along the Little Venice district.
Make the most of your medieval adventure by staying in historic boutique hotels or medieval inns, savoring local specialties like cassoulet, pierogi, or paella, and exploring cities through guided walking tours led by knowledgeable locals.
These cities invite you to walk through history. Sort your itinerary, wear your comfy walking shoes, and enjoy the medieval world when you stay there. What city will you visit first? Start planning and share your top pick.
Disclaimer: This list is solely the author’s opinion based on research and publicly available information.
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