A fairytale cityscape with cobbled streets, medieval towers, and centuries of stories.
Tallinn’s Old Town is one of the best-preserved medieval city centers in Europe, and it truly feels like stepping into a storybook. Whether you’re into architecture, history, food, or just wandering charming alleys, this area will enchant you. Here are 10 things you can’t miss when exploring Tallinn’s magical Old Town.
1. Climb to Toompea Castle and Stroll Along the Castle Walls
Perched atop Toompea Hill, this historic castle dates back to the 13th century and still houses the Estonian Parliament today. While you can’t explore the building’s interior freely, the area around it is rich with history, and ideal for photos. Walk the nearby castle walls and admire the centuries-old towers.
2. Visit the Majestic Alexander Nevsky Cathedral
Just across from Toompea Castle sits this striking Russian Orthodox cathedral with its black onion domes and golden crosses. Inside, you’ll find elaborate mosaics and an atmosphere of quiet reverence. It’s a dramatic contrast to the Gothic architecture surrounding it.
3. Soak in the Views from Kohtuotsa and Patkuli Viewing Platforms
Tallinn has postcard-perfect viewpoints, and these two are the crown jewels.
Kohtuotsa gives you sweeping views of the Old Town’s spires and modern city skyline beyond.
Patkuli, meanwhile, looks over red-tiled rooftops and the harbor. Both are perfect for sunrise or golden hour.
4. Explore Town Hall Square (Raekoja Plats)
At the heart of Old Town lies this vibrant square, flanked by colorful merchant houses and the medieval Tallinn Town Hall, the oldest of its kind in Northern Europe. In summer, enjoy an outdoor café; in winter, this is where Tallinn’s famous Christmas market transforms the area into a fairytale.
5. Find the Hidden Courtyards
Behind the historic façades lie peaceful courtyards full of charm. Look for Masters’ Courtyard (Meistrite Hoov), where you’ll find craft shops, art galleries, and a café tucked into the old stone walls. These quiet pockets feel like secret gardens in the middle of the city.
6. Grab Coffee at a Medieval-Inspired Café
Old Town has no shortage of cozy cafés. Try Kehrwieder Chocolaterie, hidden in a candle-lit cellar near Town Hall Square, or RØST Bakery just outside the Old Town gates for pastries and fresh-brewed coffee. For a medieval vibe, Olde Hansa offers spice wine and period-inspired dishes.
7. Walk Through the Viru Gate
One of the iconic entrances to the Old Town, Viru Gate is flanked by two round towers and lined with flower stalls. It’s a great starting point for your Old Town journey — and an ideal photo spot.
8. Hear the Legends of Tallinn
Tallinn is full of myths and folklore. Ask a guide or read up on stories like the ghost monk of the Danish King’s Garden, the devil’s wedding at the Town Hall, or the hidden treasure beneath St. Olaf’s Church. These tales add a layer of mystery to the medieval stones.
9. Visit the Tallinn City Museum
Housed in a 14th-century merchant house, this small museum offers a fascinating look at Tallinn’s past — from medieval guilds to 20th-century revolutions. It’s a great place to understand how the Old Town grew and changed over time.
10. Get Lost (On Purpose)
Some of the best experiences come when you stop looking at the map and just wander. Peek into antique shops, duck through archways, discover street art or a sudden silence in a hidden alleyway. Tallinn’s Old Town is meant to be explored slowly.
Final Tip
Wear comfortable shoes — the cobblestones are beautiful, but they’re no joke for your feet. And try to explore early in the morning or at twilight, when the streets are quieter and the magic is even stronger.
Whether it’s your first visit or your fifth, Tallinn’s Old Town never gets old.