• St. Nicholas’ Church and Museum - Discover the tale of the 1944 Soviet carpet bombing of Tallinn, a tragic event that rendered half of the city homeless and destroyed a tenth of the medieval Old Town.
• Freedom Square - Uncover the rich history of central Freedom Square and Estonia’s Monument to the War of Independence.
• Kiek in de Kok and Bastion Passages Museum - Explore the town walls, towers, and fortifications, and learn how Tallinn became an impregnable medieval fortress never conquered by force.
• Danish King’s Garden - Stroll along the town walls, towers, and fortifications, and discover how Tallinn became an impregnable medieval fortress never conquered by force.
• Alexander Nevsky Cathedral - Visit the city’s most debated church — an imperial addition in the heart of Old Town.
• Toompea Castle - Delve into Estonia’s historic seat of power, where numerous rulers have governed since the 12th century.
• St Mary’s Cathedral - Enter the iconic cathedral and admire walls adorned with original Coats of Arms from noble families dating back to the 17th century.
• Viewing Point Kohtuotsa - Enjoy breathtaking views of both medieval and modern Tallinn from the city’s best panoramic viewpoint.
• Long Boot (Pikk Jalg) - Discover how Tallinn once existed as two rival cities, filled with feuds and tension, as you cross from one historic city to the other.
• Great Guild Hall - Witness Gothic buildings unchanged since the 15th century and hear stories of Tallinn’s influential medieval trade guilds.
• Church of the Holy Spirit Puhavaimu Kirik - Reflect on the first church that finally acknowledged the unenlightened native pagans, three centuries after the land had been converted to Christianity.
• Town Hall Pharmacy - Glimpse into Europe’s oldest continuously operating pharmacy — six centuries and counting in the very same building.
• Tallinn Town Hall - Admire the oldest surviving medieval Town Hall in Northern Europe, standing unchanged since 1404.
• St. Catherine’s Passage - Wander down one of the Old Town’s most atmospheric medieval alleys and view the ruins of Northern Europe’s largest medieval cathedral.

• Free starting point anywhere in the Old Town
• Entrance fees

• Gratuities

Explore the medieval charm of Tallinn’s Old Town with a knowledgeable local guide on this captivating, customized private walking tour. Experience genuine stories, personal anecdotes, fresh humor, and honest insights without any unnecessary fluff or wasted time.

This tour is perfect for those who are weary of crowded group tours and guides reciting memorized scripts. If you seek true authenticity—no scripted speeches or umbrellas in the air—this is the experience for you. Enjoy the company of a passionate native guide eager to reveal the real Tallinn, up close and personal.

• Private and comprehensive 2½ - 3½ hour guided walking tour of Tallinn Old Town
• Discover key highlights such as Town Hall Square, scenic viewpoints, and hidden treasures
• Flexible tour duration and pace tailored to your interests
• Engaging narratives, intricate storytelling, and a broad perspective
• Friendly, knowledgeable native guide offering local insights and personal stories
• Pet friendly
• Distance: 2.5–3 km walk through both Lower and Upper Old Town; port pickup adds an additional 1 km.

For a full refund, cancel at least 24 hours before the scheduled departure time.