10 Enchanting Medieval Towns and Cities for a Romantic Valentine’s Weekend Break

As Valentine’s Day approaches, many couples seek a retreat to celebrate their love in a setting that exudes charm and romance.

For those enchanted by history and the allure of old-world charm, medieval towns and cities offer an ideal backdrop for a romantic getaway. Picture cobblestone streets, ancient architecture, and a whimsical atmosphere straight out of a fairytale.

Here are ten fairytale medieval towns and cities around the world perfect for a memorable Valentine’s weekend break.

1. Bruges, Belgium

Known as the “Venice of the North,” Bruges boasts picturesque canals, medieval buildings, and cobblestone streets. Couples can wander hand in hand through the Markt square, visit the romantic Minnewater Lake, and indulge in delectable Belgian chocolates.

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2. Rothenburg ob der Tauber, Germany

This well-preserved medieval town is a haven for couples seeking romance. Take a stroll along the charming city walls, explore the narrow streets lined with half-timbered houses, and share a kiss beneath the clock tower of the Rathaus.

3. Annecy, France

Nestled in the French Alps, Annecy is often referred to as the “Venice of the Alps” due to its network of canals and stunning scenery. Couples can enjoy boat rides on Lake Annecy, wander through the old town’s pastel-colored buildings, and savor French cuisine at intimate restaurants.

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4. Sintra, Portugal

With its fairytale castles, lush gardens, and winding streets, Sintra is a romantic escape steeped in history. Explore the whimsical Pena Palace, stroll hand in hand through the romantic gardens of Quinta da Regaleira, and watch the sunset from the cliffs of Cabo da Roca.

5. Tallinn, Estonia

Tallinn’s medieval old town transports visitors back in time with its well-preserved city walls, cobbled streets, and Gothic architecture. Couples can climb the spire of St. Olaf’s Church for panoramic views, cozy up in a quaint café, and explore hidden courtyards and alleyways.

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6. Colmar, France

Located in the heart of the Alsace wine region, Colmar is a postcard-perfect medieval town known for its colorful half-timbered houses and flower-lined canals. Couples can meander through the charming streets, sample local wines, and share a romantic dinner in one of the town’s cozy restaurants.

7. Roquebrune-Cap-Martin, France

Tucked away on the French Riviera, Roquebrune-Cap-Martin is a medieval gem overlooking the sparkling Mediterranean Sea. Couples can explore the narrow streets of the old town, stroll through lush gardens, and admire panoramic views from the ancient castle ruins.

8. Cesky Krumlov, Czech Republic

With its fairy-tale castle perched above the Vltava River, Cesky Krumlov is a romantic destination straight out of a storybook. Couples can wander through the charming old town, take a leisurely boat ride along the river, and enjoy a candlelit dinner in a historic tavern.

9. Siena, Italy

Known for its medieval architecture, historic palaces, and vibrant piazzas, Siena is a romantic destination in the heart of Tuscany. Couples can climb the Torre del Mangia for panoramic views, explore the winding streets of the old town, and share a kiss in the shadow of the magnificent Duomo.

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10. Hallstatt, Austria

Nestled beside a tranquil lake and surrounded by majestic mountains, Hallstatt is a picture-perfect medieval village straight out of a storybook. Couples can stroll along the lakeside promenade, explore the charming alleys lined with pastel-colored houses, and take a romantic boat ride on Lake Hallstatt.

Each of these fairytale medieval towns and cities offers a romantic escape where couples can create unforgettable memories amidst historic charm and timeless beauty.

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Whether it’s wandering hand in hand through cobblestone streets, sharing a kiss beneath ancient towers, or simply savoring each other’s company in a cozy café, these destinations provide the perfect backdrop for a magical Valentine’s weekend break.

10 Great Websites Where You Can Book a Romantic Valentine’s Weekend Break to a Medieval Town or City


These websites offer a wide range of accommodation options, including hotels, bed and breakfasts, vacation rentals, and more, allowing you to find the perfect place for a romantic getaway to a medieval destination. Happy booking and enjoy your Valentine’s weekend break!