Tallinn: Old Town Private & Personalized Walking Tour

This experience is designed for those who have had enough of impersonal, overcrowded tours and guides reciting stale, memorized monologues. If you are searching for genuine connection and authenticity — free from rehearsed jokes and waving flags — then this is the tour for you.

Immerse yourself in a deep, engaging exploration led by a passionate local guide who is eager to share the true essence of Tallinn in an up-close and personal way. Throughout the journey, you will be shown a curated portfolio of historical photographs, archival videos, and period paintings, providing fascinating visual context and bringing the city’s layered past to life at every stop.

You can meet your guide in front of the Tourist Information Center at Niguliste 2, or he can conveniently collect you from your accommodation anywhere within the Old Town.

Your exploration begins at Harju Street beside St. Nicholas’ Church, where you will hear the gripping account of the devastating 1944 Soviet carpet bombing — a terror attack that left up to half of Tallinn’s population homeless and destroyed a full tenth of the medieval Old Town.

Next, delve into the complex history and buried narratives of Freedom Square and Estonia’s poignant Monument of Independence.

Walk in the shadow of the formidable medieval town walls, towers, and fortifications — such as Kiek in de Kök and the Danish King’s Garden — and learn how Tallinn evolved into an impregnable fortress that was never successfully conquered by force.

Visit the opulent Alexander Nevsky Cathedral, the city’s most politically charged church, erected as a powerful symbol of imperial rule in the very heart of the Old Town.

Ascend Toompea Hill to explore Toompea Castle, Estonia’s historic seat of power, where authority has been wielded continuously since the 12th century.

Step inside the iconic St. Mary’s Cathedral to admire its walls, which are adorned with original coats of arms belonging to 17th-century nobility.

Soak in breathtaking, sweeping views that encompass both the medieval spires and modern skyline of Tallinn from the city’s premier panoramic viewpoint.

Learn how Tallinn once functioned as two rival cities, locked in constant feud, as you cross from one historic district to the other via the famous Long Leg Street.

Marvel at Gothic buildings that have remained virtually unchanged since the 15th century and hear tales of influential medieval merchant brotherhoods at the historic Great Guild Hall.

Pause at the Holy Spirit Church — notable for being the first to finally acknowledge Estonia’s indigenous pagan heritage, centuries after the Baltic Crusades.

Peek into the Raeapteek, Europe’s oldest continuously operating pharmacy, which has been dispensing remedies from the same building for over six centuries.

Admire the oldest surviving medieval Town Hall in all of Northern Europe, a magnificent structure that has dominated Town Hall Square since 1404.

Finally, meander down St. Catherine’s Passage, one of the Old Town’s most enchanting and atmospheric medieval lanes, where you can glimpse the solemn ruins of what was once Northern Europe’s largest medieval cathedral.

We will conclude at a convenient location in the central Old Town, leaving you with honest, local advice and personalized tips on where to eat, drink, shop, and wander — so you can continue discovering Tallinn on your own, well-equipped with genuine insider knowledge.