Year-round
Dates
1.5h
Duration
2+
Min group size

The Scandalous Medieval Tallinn Old Town Tour

The Scandalous Medieval Tallinn Old Town Tour reveals the darker and more provocative side of medieval city life. This walking tour through the lower Old Town focuses on crimes, punishments, hidden relationships, and stories that rarely appear in traditional history books.

Highlights of the tour:

  • Discover medieval crimes and brutal punishments
  • Learn about the life of the town executioner
  • Hear stories of epic feasts and drinking traditions
  • Explore scandals, forbidden relationships, and prostitution
  • Understand strict church regulations and social rules of the time

Medieval Tallinn had different restrictions and rules of conduct than those in place today. Come and see Tallinn Old Town in a completely different way!

The Scandalous Medieval Tallinn Old Town Tour offers a different perspective on the city’s past. Instead of focusing on architecture and political history, this walk brings attention to the social realities of medieval life.

In medieval Tallinn, daily life was regulated by strict rules. Punishments were public, discipline was harsh, and moral standards were tightly controlled by both authorities and the church. The town executioner played an essential but often feared role in society, while public humiliation and corporal punishment were common forms of justice.

At the same time, medieval Tallinn was far from dull. The city was known for lively feasts, heavy drinking, and complicated relationships. Lovers, prostitutes, and secret affairs existed alongside rigid church rules and bizarre moral expectations.

This tour explores the lower part of Tallinn Old Town and presents historical facts in a direct and honest way, offering a more complete picture of medieval urban life.

PS! This walking tour is not suitable for children.

PRICE INCLUDES: guide service

TOUR START: Viru gates. Time as agreed.

TOUR END: Freedom square

LANGUAGES: English

1

Viru Gates and introduction to medieval city life

Meet your guide at the Viru Gates and step into the lower part of Tallinn Old Town. Get an introduction to the social rules, moral codes, and bizarre regulations that shaped everyday life in medieval Tallinn. Discover how strict norms governed behaviour — and what happened when someone crossed the line.
2

Dominican Monastery and the secrets of the Great Guild

Walk past the Dominican Monastery and hear how monasteries functioned as strict religious centres, yet were deeply connected to city life. Learn about monks as unexpected “therapists” and the dramatic events that unfolded in the Great Guild — from epic celebrations to chaotic wedding feasts that spiralled out of control.
3

Town Hall area and medieval justice

Explore the area around Town Hall Square, where public humiliation and punishment were once part of everyday life. Hear about gruesome murders, torture sentences, and the difficult role of the town executioner. Discover what could get you tied to the pillory and which crimes led to the harshest consequences.
4

Town Hall area and medieval justice

The tour ends near Freedom Square, reflecting on how medieval restrictions, scandals, and punishments shaped Tallinn’s identity. See the Old Town from a completely different perspective — through the lens of its most controversial stories.
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Optional tips to enhance your experience:

  • let us give you hints on where to find the most authentic Estonian handicraft shops and restaurants serving Estonian food;
  • we can organize a lunch/dinner for your group

Prices for The Scandalous Medieval Tallinn Old Town Tour

This activity is not suitable for kids!

The minimum group size for our tours is two people. Solo travellers are welcome to join others. Send the request with possible dates, and we will give you more information.

The price per person is based on your group size.

Number of participants: Price per person:
1 joining others or price for 2
2-3 43 euros
4 33 euros
5-10 23 euros
11 and more on request

Tour Reviews

17. Nov 2025

We went on this interesting tour of Old Tallinn with Stassi – what fascinating facts and thought-provoking stories. We were able to discuss in a small group and ask more questions. Memorably emotional, I recommend it!

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