The highlights of Tallinn, Estonia

Tallinn is an interesting combination of traditional Medieval city and post-Soviet hipster oasis. The marriage of the two is somewhat disjointed, but it definitely works. The city is interesting, historical, and ultra hip.

Tallin’s Old Town

Tallin’s Old Town area is nicely delineated because it’s completely walled in. The most picturesque entrance to the town is Viru Gate, which frames the city center with two identical towers. It has one of Europe’s best preserved fortifications and 20 defensive towers still standing. The structures are appreciated from a few different viewpoints. There’s the Nun’s Tower and Town Wall Walkway, which gives you access to the view of the center of Old Town from the towers themselves. There’s also some fantastic views from the Kohtuotsa Viewpoint and Parkuli Viewing Platform, which gives you a direct view of the Town Wall and the Nun’s tower from a perspective outside the walls of the city.

Inside, you can wander around the streets, which are so nicely maintained that everything looks like Disneyland. In the center of Old Town, you’ll find a large square with lots of restaurants, on one end of which is Tallinn Town Hall. This Gothic building is from the 13th century and if you really want to go back in time, have some elk soup and a meat pastry from III Draakon, a candlelit eatery straight out of this time period. After that, take a long walk down Pikk tanav (Long Street) and enjoy the beautiful views. Or stop at the oldest operating pharmacy in Europe, Raeapteek, established in 1422.

Aside from fortifications like Toompea Castle that you can visit, there is no shortage of churches in Tallinn’s Old Town, including St. Mary’s Cathedral, the Holy Spirit Church, St. Olaf’s (Oleviste) church and the Russian orthodox Alexander Nevsky Cathedral. For a high view of the city from inside the walls, you can climb to the top of St. Olaf’s. The sweeping views include Old Town and as far out as Tallinn Bay.

The Tallinn Bay area

A good place to appreciate the less Disneyland version of the city is by Tallinn Bay. At Lennusadam Seaplane Harbour, you can see ships, old and new, that have been a part of Estonia’s history. It’s part of the Estonian Maritime Museum, a ticket to wchih gives you entry to some of the ships, including the submarine “Lembit” and the ”Suur Tõll” steam-powered ice breaker.

East of the shipyard, you’ll find Patarei Sea Fortress Prison. It has been sadly closed indefinitely, so it stands as a fantastic abandoned relic. The outside is covered in graffiti and barbed wire. At least during the warm months of the year, you can walk around behind it along the Beeta Promenade. It connects the harbor, the prison and Kalamaja Cemetery Park. So I guess you could call this the haunted promenade of Tallinn. Though it’s frequented by plenty of families, runners, and people with dogs.

East still of Paterei is Linnahall, a giant concrete amphitheater built for the Moscow Olympics during the Soviet era. Like all Soviet structures, it’s a hideous mess of concrete. But it’s been repurposed by locals as a site for graffiti, music, and hanging out to enjoy good weather. There’s broken glass all over the place, but I was surprised how many people were hanging out there on a Saturday afternoon. Even people with toddlers.

The hipster Tallinn

I’ve saved the best for last, and that’s Telliskivi. The area, intentionally on the wrong side of the tracks in an old industrial complex, is one of the coolest hipster oases I’ve seen outside of Berlin. The area has the brick and metal look of an old warehouse district splashed with colorful murals. Outdoor restaurants in old shipping containers are lit up in the evening by string lights.

In Telliskivi, you’ll find locals watching animated films projected on the side of a run down building on a Saturday night. It’s full of galleries, studios, craft beer pubs, boutique specialty shops, and hipster restaurants. Try the gin and rose lemonade cocktail at Trühvel, but dine at Kivi Paber Käärid (Rock, Paper, Scissors), which is somehow both healthy and decadent.

For all its different neighborhoods and the unique environments they create, Tallinn is going on the top of my list of places I want to return to.

Get the GPS-guided version of this and other Tallinn guides on GPSmyCity here.