Tales of Old Tallinn 2-hour Walking Tour - Starting at Tallinn Town Hall: The Heart of Old Town

Tales of Old Tallinn 2-hour Walking Tour

Explore Tallinn's medieval past with the Tales of Old Tallinn 2-hour walking tour, featuring historic sites, legends, stunning viewpoints, and engaging storytelling.

Discover Tallinn’s Medieval Charm in Just 2 Hours

Tales of Old Tallinn 2-hour Walking Tour - Discover Tallinns Medieval Charm in Just 2 Hours

The Tales of Old Tallinn 2-hour walking tour offers an engaging glimpse into Estonia’s capital city’s medieval past for only $41.58 per person. With a 5.0/5 rating from 36 reviews and recommended by 100% of participants, this tour stands out as a favorite among visitors. Its approximate 2-hour duration makes it an ideal option for those seeking a quick yet rich cultural experience. The tour is designed for most travelers, involves around 2 km of walking, and features a mobile ticket for convenience. It departs from Tallinn Town Hall, and groups are limited to 20 participants, ensuring an intimate and personal atmosphere.

This walking journey is perfect for history enthusiasts and curious explorers who enjoy stories that bring old buildings and legends to life. The tour avoids boring dates and unknown names, focusing instead on fascinating stories and legends that still influence Tallinn today. While the tour covers many highlights, it is recommended to dress warmly in winter, as outdoor conditions can be cold.

Key Points

Tales of Old Tallinn 2-hour Walking Tour - Key Points

  • Two hours of storytelling covering Tallinn’s medieval history and legends
  • Affordable price of $41.58, with many reviews praising the value
  • Visits to key sites including Tallinn City Hall, Alexander Nevsky Cathedral, and Patkuli Viewpoint
  • Expert guides, such as Maria and Max, who weave historical facts into compelling narratives
  • Stunning viewpoints of Tallinn’s rooftops from Kohtuotsa and Patkuli platforms
  • Flexible stops like cafes and old trading spots, offering authentic local atmosphere

Starting at Tallinn Town Hall: The Heart of Old Town

Tales of Old Tallinn 2-hour Walking Tour - Starting at Tallinn Town Hall: The Heart of Old Town

The tour kicks off at Tallinn Town Hall on Raekoja plats, the central square of Old Town. This historic site has long been the hub of Tallinn’s political life, where court decisions and city meetings took place. The guide explains how decisions affecting the entire city were made here and shares tales about the square’s history, including why only two people were executed in this space over centuries. Admission to the Town Hall itself costs 5 EUR, but it’s not included in the tour price.

This starting point offers a lively atmosphere and immediate insight into Tallinn’s governance. The guide’s storytelling makes the square come alive, emphasizing its importance in medieval times and its role as a community gathering spot. This location sets the tone for the rest of the tour, blending historical facts with engaging legends.

The Mysteries of Rataskaevu Street and the Cat’s Well

Tales of Old Tallinn 2-hour Walking Tour - The Mysteries of Rataskaevu Street and the Cats Well

From the main square, the tour continues to Rataskaevu Street, home to the Cat’s Well, an unusual medieval wheel well. Visitors can listen for whispers of evil water spirits, as legends suggest these spirits still linger in the well’s depths. The 5-minute stop here is free, and it offers a glimpse into Tallinn’s folklore and the city’s well-preserved medieval water infrastructure.

Next, the guide leads visitors to St. Nicholas’ Orthodox Church, one of the oldest churches in Tallinn, built in the 13th century. Though admission is not included, viewing the church from outside reveals its historical significance as a communal meeting place for centuries. The guide shares stories about the church’s role in city life, adding depth to its impressive exterior.

The Unique Shortcut: Lühike Jalg

Tales of Old Tallinn 2-hour Walking Tour - The Unique Shortcut: Lühike Jalg

A short 5-minute walk from the church brings the group to Lühike Jalg, the shortest route connecting the Lower and Upper Old Town. Used solely by pedestrians, this narrow passageway highlights Tallinn’s medieval urban design. Its preservation offers a tangible link to the past, and the guide explains its strategic importance and use during medieval times.

Danish King’s Garden and the Danish Flag Connection

Tales of Old Tallinn 2-hour Walking Tour - Danish King’s Garden and the Danish Flag Connection

The Danish King’s Garden provides a 10-minute stop to explore a garden connected to Estonia’s Danish history. Visitors learn about its link to the Danish flag and the celebration held there every June 15th, which continues in modern times. The garden’s unique character and historical tie make it a notable highlight for history buffs.

The Political Heart: Estonia’s Parliament Building

Tales of Old Tallinn 2-hour Walking Tour - The Political Heart: Estonia’s Parliament Building

While not a medieval structure, the parliament building in Tallinn remains central to Estonia’s ongoing political life. This site marks the transition from medieval origins to contemporary governance, reminding visitors of Tallinn’s continuous role as the nation’s political hub.

Alexander Nevsky Cathedral: The Russian Orthodox Icon

Tales of Old Tallinn 2-hour Walking Tour - Alexander Nevsky Cathedral: The Russian Orthodox Icon

The Alexander Nevsky Cathedral stands out for its rich decoration and Russian Orthodox architecture. Built primarily for political reasons, it features Tallinn’s largest bell, weighing around 15 tonnes. If timing permits, visitors might hear its resonant chime, adding a memorable auditory experience to the sightseeing.

St. Mary’s Cathedral and the Swedish Royal Connection

Next, the tour visits St. Mary’s Cathedral, distinguished by its simple exterior yet significant historical interior. It houses the gravestone of a Swedish king’s daughter, connecting Tallinn to regional royal history. Admission is 5 EUR, but visiting is optional, allowing flexibility for those interested in exploring further.

The Best Views: Patkuli and Kohtuotsa Viewpoints

Two spectacular viewpoints offer panoramic sights of Tallinn’s rooftops. Patkuli Viewpoint provides a 10-minute stop where photographers can capture stunning images and listen to stories about the city’s skyline. The Kohtuotsa Viewing Point offers a north-facing perspective of Toompea Hill, with views of red roofs and the modern parts of Tallinn. Visitors are encouraged to revisit these spots in different seasons for contrasting perspectives.

The Long Path to the Upper Town

The longest way used to access the Upper Town was mainly for horse transport. This historic route remains well-preserved and offers a tangible sense of medieval travel in Tallinn. The guide details its significance and how it shaped the city’s development.

Cafés and Trading Spots: Cafe Maiasmokk and the Town Hall Pharmacy

Stopping at Cafe Maiasmokk, the oldest café in Tallinn, provides a 10-minute break to enjoy historic interiors that haven’t changed since the 19th century. This café’s ambiance makes it a favorite for those wanting a taste of local tradition.

The Town Hall Pharmacy, the oldest continually operating pharmacy in Europe since the 15th century, opens up stories about medieval medicine and commerce. It’s an interesting stop for those curious about historical trades and local health practices.

Medieval Monasteries and the Oldest Trading Place

The Katariina Käik, a 13th-century monastery, remains well-preserved and is a hidden treasure on the tour. It housed medieval monks who studied and prayed, offering a quiet, contemplative space. Visiting this site is optional, with a 5 EUR admission.

The tour concludes at Vanaturu Kael, the oldest trading place in Tallinn, which later moved to the Town Hall Square. This spot highlights Tallinn’s longstanding role as a trading city and wraps up the tour with a sense of historical continuity.

Overall Experience and Guide Quality

Throughout the tour, guides such as Maria and Max earn high praise for their deep knowledge and friendly demeanor. They skillfully intertwine historical facts with legends, making each site memorable. Visitors note the well-paced route, designed to cover major sights without feeling rushed, even in colder weather.

The tour offers good value considering the rich stories, viewpoints, and historic sites visited. Some feedback mentions the price of 50 EUR as slightly high but is balanced by the quality of storytelling and personalized attention from the guides.

Practical Tips and Considerations

Participants should dress warmly during winter since outdoor stops are frequent and outdoor weather can be cold. The tour involves around 2 km of walking, so comfortable footwear is recommended. The meeting point at Tallinn Town Hall is accessible via public transportation, and the tour is suitable for most travelers.

Admission fees for certain sites, such as St Mary’s Cathedral (5 EUR) and Town Hall (5 EUR), are not included in the ticket price. The tour’s flexibility means visitors can choose to visit these sites on their own if interested.

Final Thoughts on the Tales of Old Tallinn Tour

The Tales of Old Tallinn 2-hour walking tour offers a rich, story-driven experience that brings Tallinn’s medieval streets and legends to life. With expert guides, stunning viewpoints, and engaging narratives, it suits history lovers and those keen to experience the city’s soul in a short time.

Its affordable price and small group size make it a compelling option for anyone wanting an authentic, informative stroll through Tallinn’s past. While some logistical details, like optional site visits, require planning, overall this tour provides great value and memorable stories that will resonate long after leaving.

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Tales of Old Tallinn 2-hour Walking Tour



5.0

(36 reviews)

94% 5-star

“Maria was a great tour guide. She was very knowledgeable and took us to many parts of Tallinn. Highly recommend this tour!”

— Julie Y, Jun 2025

Frequently Asked Questions

Is this tour suitable for all ages?
Yes, most travelers can participate, but it involves around 2 km of walking, so comfortable footwear and some mobility are recommended.

Are admission fees to sites included?
No, fees for places like St Mary’s Cathedral and Town Hall are not included. These are paid separately if visitors wish to explore inside.

What is the meeting point?
The tour starts at Tallinn Town Hall on Raekoja plats, the central square of Old Town.

How long does the tour last?
The entire experience is about 2 hours, covering many highlights of Tallinn’s medieval history.

Is the tour suitable in winter?
Yes, but visitors should dress warmly, as outdoor stops and weather conditions can be cold.

Can I cancel this tour?
Yes, free cancellation is available up to 24 hours before the scheduled start.

How many people typically join the tour?
The group size is limited to 20 travelers, ensuring a personalized experience.

What makes this tour stand out?
Its focus on legend and storytelling, combined with stunning viewpoints like Patkuli and Kohtuotsa, makes it a memorable way to explore Tallinn’s past.

Are the guides knowledgeable?
Absolutely. Guides like Maria and Max are highly praised for their deep historical knowledge and engaging narration.

Is the tour worth the price?
Considering the quality of storytelling, the variety of sites visited, and the views offered, the price of $41.58 provides good value for a rich cultural experience.