See the heart of Tallinn, the Town Hall Square, and the surrounding open-air market, with vendor stalls, small cafes and souvenir shops. Learn about the 13th-century Holy Spirit Church, one of the oldest in the city. View the City Museum building, originally a home of the 14th century.
Ending point: Where you started
Meeting point map. Here
This tour is for you if you’re done with crowded group tours and guides droning on and on through memorized scripts. If you crave genuine authenticity — no canned jokes, no umbrellas in the air — this is your kind of experience.
Enjoy a deep dive with a passionate native guide eager to show you the real Tallinn, up close and personal. Along the way, enjoy a curated visual portfolio of historic photos, videos, and paintings, offering fascinating glimpses into the city’s layered history at each stop.
Meet your guide either in front of the Tourist Information Center at Niguliste 2, or have him collect you from your accommodation anywhere in the Old Town.
Begin your tour at Harju Street and St. Nicholas’ Church, where you’ll hear the gripping story of the devastating 1944 Soviet carpet bombing — a terror attack that left up to half of Tallinn homeless and destroyed a tenth of the medieval Old Town.
Next, uncover the layered history and buried secrets of Freedom Square and Estonia’s Monument of Independence.
Stroll beneath the medieval town walls, towers, and fortifications — like Kiek in de Kök or the Danish King’s Garden — and discover how Tallinn became an impregnable medieval fortress never conquered by force.
Visit Alexander Nevsky Cathedral, the city’s most controversial church and an imperial imposition in the heart of Old Town.
Explore Toompea Hill and Toompea Castle, Estonia’s historic seat of power, where rulers have governed since the 12th century.
Step inside the iconic St Mary’s Cathedral and admire walls adorned with original noble coats of arms from the 17th century.
Soak in sweeping views of both medieval and modern Tallinn from the city’s best panoramic viewpoint.
Learn how Tallinn once existed as two rival cities, with constant feuds and tension, as you cross from one historic city to the other via the famous Long Leg Street.
Marvel at Gothic buildings unchanged since the 15th century and hear tales of powerful medieval guilds at the Great Guild Hall.
Pause at the Holy Spirit Church — the first to finally remember Estonia’s “unenlightened” pagans, centuries after the Baltic Crusade.
Peek into Europe’s oldest continuously operating pharmacy — still in the same building after six centuries.
Admire the oldest surviving medieval Town Hall in Northern Europe, standing unchanged since 1404 on Town Hall Square.
Finally, stroll down St Catherine’s Passage, one of the Old Town’s most atmospheric medieval alleys, and glimpse the ruins of Northern Europe’s largest medieval cathedral.
