The Baltic region is full of charming port cities — many in countries that were former republics of the Soviet Union — and the capital of Estonia is certainly one that’s not to be missed. Tallinn’s fairytale-like, red-roofed Old Town sits in stark contrast to its more modern glass-and-steel counterpart, and is easily explored on foot in a single day.
What We Love
The Town Wall: Tallinn’s medieval stone wall still surrounds Old Town — with an impressive regiment of 20 of the original 46 defense towers still standing.
Patkuli Viewing Platform: Get your selfie stick ready: This platform on the north side of Toompea hill offers perfect views of the town wall and several of its 125-foot-tall defense towers.
Kiek in de Kök: Located in one of Old Town’s medieval towers, this museum houses a collection of cannons and weapons, and offers access to tours of the Bastion Passages, military tunnels that run beneath Toompea hill.
Best Known For
Historic Churches: Tallinn’s Old Town has five notable churches dotting its skyline. Don’t miss onion-domed St. Alexander Nevsky Cathedral, the medieval-meets-Baroque Cathedral of St. Mary the Virgin, and the soaring black spire of Gothic-style St. Olav’s, said to be the world’s tallest building from 1549 to 1625.
Town Hall Square: The heart of Tallinn, this eight-centuries-old square is lined with historic merchant houses and vibrant cafes. You'll find open-air concerts and handicrafts markets in the summer, and come December the town’s Christmas tree, a tradition that dates back more than 500 years.
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Who It's Best For
Photo Buffs: Tallinn is ready for its close-up. Anyone with an eye for a great shot can simply wander and discover an incredible Instagram moment around every corner.
Don't Say We Didn't Warn You
It can get crowded: Everyone wants to see the sights of Old Town, which can feel highly congested when two or more large ships are in port.
Donna Heiderstadt is a New York-based contributor to ShermansCruise who has also written for Coastal Living and Islands.