A Stroll Through Medieval Tallinn

If you asked people to name their ideal city for a few days’ visit, I doubt that many people would say Tallinn… but they should! While people are obsessing over Paris, Rome and Barcelona, they are missing out on one of Europe’s best preserved Medieval cities.

While the Estonian capital may not stand alongside Rome and Paris yet in the list of city break destinations, it is gradually developing its statues as a visitor’s stop.

Tallinn can be reached directly from London Stansted with Ryanair, and also has ferry links with Helsinki to the north and Stockholm to the west.

Tallinn was founded as a city in 1248 and for much of its history, has served as a capital city under foreign control. Estonia was part of the Russian Empire during the era of the Russian Tsardom and following the Revolution in 1917, automatically became a satellite state of the communist USSR. It was not until August of 1991 that an independent Estonia was born. Ever since relinquishing the Soviet weight which for so long had weighed it down, Estonia has since developed a growing economy and tourist industry.

My visit to Tallinn was in June 2016, and it left quite an impression on me. I began my exploration of the city outside of the Alexander Nevsky Cathedral.

Tallinn’s Alexander Nevsky Cathedral

Built between 1894 and 1900, the cathedral is a quintessential example of Russian Revival architecture. Named in honour of the eponymous victor of the Battle of the Ice, the cathedral was designed by Mikhail Preobrazhensky during the Tsardom’s period of ‘Russification’, whereby Russia attempted to make everything within its territory overtly Russian in an attempt to express dominance and national pride. For this reason, Estonians initially held the cathedral in contempt, believing it represented Russian control and oppression over the country.

Despite its purpose as a symbol of Russian authority, the cathedral is still a beautiful example of architecture and is worthy of a couple of holiday photos during your visit.

After the cathedral, I took a short walk through the tight cobbled streets of Tallinn’s old town to reach a viewpoint where it is possible to afford a view across the lower section of the old town.


From this point, two interesting points about the city can be observed. For one, you can see how small and compact it is. With a population of just over 440,000, it is easy to forget that this is an European capital city that you find yourself in. Secondly, how beautifully medieval this capital city is. From the vantage point, I had a view across Tallinn’s brown-tiled roofs, interspersed by church towers and spires which can only be European.

From the viewpoint, I descended down a narrow alleyway into the lower half of the old town; towards the main market square.


During my summer visit, a performance stage was set up in the main square, with local traders selling their crafts and produce at their stalls around the square. The city’s medieval heritage is most prominent here. The old town has managed to beautifully preserve its archaic buildings, resisting the Soviets’ desire for filling cities with ugly concrete structures. Restaurants decorated in medieval style, with their staff members dressed up as knights and dames embraces the city’s heritage. The old city walls are nearby to the square, marking where the original gates to Tallinn once stood.

Tallinn’s old town square, with its summer market stands

There are a series of narrow streets off-shooting away from the main square, each worth a wander to see where you end up. That’s the beauty of Tallinn. You can let your feet wander where they like, knowing that you’ll be safe and eventually end up looking at a building or a statue harking back to its medieval age. There are no cars, no fumes and none of the usual city antics in the old town, just a labyrinth of charming cobbled streets waiting to be explored.

I eventually arrived at a street called St. Catherine’s Passage. Perhaps one of the narrowest streets in Tallinn, this passage harks back to the medieval age.


Lined on one side, you will find a selection of tourist shops and cafes, and on the other, a rather unusual wall. Several huge tombstones, each constructed in the medieval age, are attached to the wall of the street. The text etched onto the stone is fading; some more than others, but where else can you see and touch a medieval relic on the side of a street?

Medieval tombstones in Tallinn’s St Catherine’s Passage

Next time you’re considering a city break, bear Tallinn in mind and place it high on that ol’ travel list. If you’re in Scandinavia, pencil it in to your itinerary. It’s only a two hour ferry ride from Finland’s capital, Helsinki, and can also be reached by sea from the very popular Swedish capital, Stockholm.

I’m sure the charm and distinct ‘Old European’ flavour of Tallinn will leave the same impression on you as it did for me.

Estonia’s flag in the upper section of the old town

Thank you once again for reading, and feel free to get in touch.

Have you ever been to Tallinn? Let me know what you thought of it in the comments down below!

Happy travels,


P.S. All photos featured in this post were taken and are owned by myself.


8 thoughts on “A Stroll Through Medieval Tallinn

  1. thesweatergiraffe

    Haven’t been to Tallinn yet but it was recommended to me as a weekend trip so I’ll definitely be checking it out! Thanks for sharing these awesome shots and great info!!


    1. Do, you won’t be disappointed! You’re welcome, thank you for visiting and for commenting. I’ve just visited your fantastic blog. I’ve followed and am looking forward to reading more about your travels. I’d really appreciate a follow back if you could. Thanks again.

      Liked by 1 person

  2. Pingback: The Beauty of Low-Cost Airlines: Ryanair – The Part-Time Explorer

  3. Lovely post, Josh! It was great to see pictures of that wonderful city! Have you visited the Song Festival grounds? I found that whole idea fascinating. Here are links to my posts on Tallinn:
    Please check them out!


    1. Hi! Thank you for visiting and for taking the time to comment. I have not visited the Song Festival Grounds. There is so much to see in this little city and never enough time! Hopefully I will find myself there again one day.


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