Exploring Tallinn’s Medieval Old Town: A Complete Travel Guide
Tallinn’s Medieval Old Town is one of Europe’s best-preserved historic quarters, offering a storybook blend of cobblestone streets, Gothic spires, and centuries-old city walls. Whether you’re a first-time visitor or planning a return trip, this guide will help you discover the top attractions, hidden gems, and essential travel tips for making the most of your visit to Tallinn, Estonia.
For more on Estonia, check out Estonia’s best national parks, Saaremaa Island, and Estonia’s must try dishes.
1. Town Hall Square (Raekoja plats)
The Heart of Tallinn Old Town
Standing guard since 1530, a weather vane named “Old Thomas” has watched over Town Hall Square for centuries. This bustling centerpiece of the Old Town is surrounded by pastel-colored merchant houses and lively cafes. The square is home to the Tallinn Town Hall, a stunning Gothic structure built in the early 14th century.
Best time to visit: Late spring through early fall is perfect for enjoying outdoor cafes, but the square is most magical in December during the Tallinn Christmas Market, considered one of the most charming in Europe.
Travel tip: Arrive early in the morning to enjoy the quiet beauty before tour groups arrive. Don’t miss III Draakon, a medieval-themed tavern tucked into the Town Hall building.
Check out Tallinn City Tourist Office – Town Hall
2. Alexander Nevsky Cathedral
Built during the Russian Empire’s rule in 1900, the cathedral has long been a topic of debate in Estonia. Many locals once considered it a symbol of occupation, and there were even discussions about demolishing it after the country regained independence.
Perched on Toompea Hill, the Alexander Nevsky Cathedral is hard to miss with its black onion domes and ornate facade. It remains an active place of worship and one of the most iconic sights in Tallinn.
Best time to visit: The cathedral is open year-round, but spring and summer provide better light for photography.
Getting there: It’s a short uphill walk from the Town Hall Square. Look for signs to Toompea.
Travel tip: Visit early in the morning to avoid crowds and respect the no-photo policy inside.
Check out Alexander Nevsky Cathedrals official page here.
3. Toompea Hill
Toompea has been shrouded in Estonian folklore, with legends of giants and mythical kings associated with this ancient hill.
Today, it’s home to the pink baroque Estonian Parliament building and Toompea Castle. The area offers several panoramic viewpoints (like Kohtuotsa and Patkuli) that are Instagram favorites.
Best time to visit: Sunrise and sunset for golden light and sweeping views.
Getting there: From Old Town, take the Pikk jalg or Lühike jalg paths uphill.
Travel tip: Don’t rush—explore the quiet lanes and check out the quaint Alexander Nevsky gift shops and small cafes.
4. St. Olaf’s Church
This medieval church has been struck by lightning over ten times throughout its turbulent history.
St. Olaf’s Church was once believed to be the tallest building in the world during the 16th century. Its spire reaches over 120 meters and offers a panoramic lookout over the city.
Best time to visit: The tower is open seasonally, usually from April to October.
Getting there: Located on Lai Street, just a short walk from the Town Hall.
Travel tip: Be prepared for a steep climb up a narrow spiral staircase, but the view is worth every step.
5. The City Walls & Towers
At its peak, the city wall featured 46 defensive towers, of which about 20 remain today.
Tallinn’s medieval city walls are among the best preserved in Europe. Several sections are open to visitors, including the iconic Kiek in de Kök (“Peek into the Kitchen”) tower, which now houses a museum.
Best time to visit: Early autumn for fewer crowds and beautiful fall colors.
Getting there: Entry points are scattered around Old Town; the Hellemann Tower and walkway near Viru Gate is a good starting point.
Travel tip: Wear sturdy shoes and take your time on the uneven steps. The museum inside Kiek in de Kök is excellent for history buffs.
6. The Great Guild Hall
During Tallinn’s Hanseatic heyday, the Great Guild Hall hosted lavish feasts and grand balls that defined the city’s elite social life.
This historic building once hosted Tallinn’s powerful merchant guild. Today, it serves as part of the Estonian History Museum, with exhibits ranging from Hanseatic trade to local artifacts.
Best time to visit: Open year-round; great for a rainy day activity.
Getting there: Located on Pikk Street in Lower Town.
Travel tip: Look out for temporary exhibitions that often cover surprising aspects of Estonian life.
7. Kalamaja & Seaplane Harbour
Originally a fishing village, Kalamaja later became a key residential district during the Soviet era, known for its wooden architecture.
Now a bohemian hotspot, Kalamaja is filled with indie shops and cafes. Nearby, the Seaplane Harbour (Lennusadam) is one of Europe’s most impressive maritime museums.
Best time to visit: Late spring through summer for outdoor seating and events.
Getting there: A 15-20 minute walk from Old Town, or take tram line 1 or 2.
Travel tip: Try the fish & chips at the market near the harbor and relax by the sea.
8. Hidden Courtyards & Secret Passages
Many courtyards in Tallinn were once communal spaces shared by multiple families during the Soviet period.
Today, these tucked-away gems offer cozy cafes, artisan shops, and peaceful retreats from the main streets. St. Catherine’s Passage is especially picturesque.
Best time to visit: Early morning or late afternoon for solitude.
Travel tip: Visit the Masters’ Courtyard for handmade souvenirs and local chocolate.
9. Museums and Galleries
Some of Tallinn’s museums are housed in buildings over 500 years old, adding an extra layer of authenticity to their collections.
Beyond the better-known institutions, Tallinn features unique cultural sites like the Museum of Occupations and Freedom and the Tallinn City Museum.
Best time to visit: Year-round; perfect for cold or rainy days.
Travel tip: Many museums offer combo tickets or discounts with the Tallinn Card.
10. Medieval Dining in Tallinn
At Olde Hansa, every dish is prepared using only ingredients available in the 15th century—you won’t find potatoes or tomatoes on the menu.
For a truly immersive experience, dine at one of Tallinn’s medieval-themed restaurants like Olde Hansa or III Draakon. Enjoy dishes like elk stew, honey beer, and almond pastries, all served by candlelight.
Best time to visit: Dinner time for the full medieval ambiance.
Travel tip: These restaurants are popular, especially in summer and around Christmas—reserve ahead if possible.
Check our Olde Hansa’s menu here
Final Thoughts
Exploring Tallinn’s Old Town is like walking through a living museum. Its rich history, preserved architecture, and hidden corners make it one of the most enchanting travel destinations in Europe. Whether you’re into photography, history, food, or simply wandering, Tallinn will leave you wanting more.here, there’s something for everyone in this enchanting part of the city.