Exploring Tallinn, Estonia: One Epic Medieval Experience

People travel for a whole variety of reasons: to explore one-of-a-kind landscapes, experience different cultures, indulge on unique delicacies, and more.

But have you ever gone on a trip in order to experience a whole other era?


Huh? What? Time Travel?! Sounds like a load of nonsense.

Not exactly. 

Of course, it’s totally impossible to hop on a plane today and land someplace where it’s 1066 CE. However, if you’re a fan of Medieval Times, it is totally possible to experience the bygone era in Tallinn, Estonia’s Old Town.

A step into Tallinn’s Old Town really is like taking a step back to the Middle Ages. Proud and mighty stone walls, gates, and watchtowers enclose most of the old city. Inside, you’ll discover countless medieval structures lining the city’s narrow, cobblestone streets. To give my claims an additional layer of credibility, I can tell you that Tallinn’s historic centre is a UNESCO World Heritage site. It is also Northern Europe’s most well preserved medieval city.

Back in October, I spent 3 days in Estonia’s capital. While in Tallinn, 1 afternoon of sightseeing in the Old Town quickly became 3 days. Sure, I’ll admit that the wildest of rainstorms prevented me from going too far out in order to explore Tallinn’s abandoned Soviet structures, but when I look back, it seems like the showers were Mother Nature’s not so subtle hints suggesting where I should be spending most of my time. Why? Because I quickly fell head over heels with the city’s historic centre, and I didn’t want to leave a single corner unexplored.

I also couldn’t cope with being more than a 25-minute walk away from Ill Draakon’s elk soup and pies. But that’s a whole other story fit for an episode of My Strange Addition.

In Tallinn’s Old Town, it truly feels like the area’s medieval architecture has seamlessly integrated with 21st century structures and features. I’m actually more than prepared to bet you a vial of unicorn horn powder that you’ll start believing that the Middle Ages didn’t quite end in Tallinn while walking down the historic centre’s cobblestone streets. (Unicorn horn powder was once sold at the Town Hall Pharmacy). They simply evolved and developed the ability to coexist with the needs and demands of the modern day world.

So if you’re after one spectacular time travel experience, here are 29 photos of Tallinn, Estonia’s Old Town in order to convince that a trip to the city’s historic centre is the ultimate Medieval Experience.


I’ve included descriptions explaining where to find the various sites in the photos too.

Tallinn, Estonia Pin

Epic Medieval Sights in Old Town Tallinn:

As you scroll through the photos, you’ll quickly discover that even the greyest of days couldn’t even begin to mask the city centre’s magnificence.

Longing for a time travel experience? Go back to the #MiddleAges in #Estonia. Read more: Click To Tweet

Simply the most beautiful cobblestone side streets.

Coastal Gate, Tallinn, EstoniaThe Great Coastal Gate still is one of the grand entrances into Tallinn’s historic centre.

The City Gates

During the Middle Ages, protective walls enclosed the Old Town. Guarded gates enabled people to enter and exit the city, and some of them still stand today (sadly, without chainmail-clad guards *sigh of disappointment*). Nevertheless, make sure to visit:

  • The Great Coast Gate (shown above)
  • Viru Gate (featured further in this post)
  • The Long Leg Gate Tower (featured further in this post)

Old Town Tallinn, Estonia

What year is it again? 2017? 1517?

Snaps of the City Walls surrounding town.

The Walls of Tallinn

If you walk along the perimeter of the Old Town, you’ll have the chance to admire and explore the well preserved remains of the city’s medieval walls. Along Gümnaasiumi, a street in the northeastern part of Tallinn’s Old Town, you can enter a small section of the walls and climb up three of the towers (Nunna tower, Sauna tower, and Kuldjala tower).

If you’ve read some of other posts, such as my Game of Thrones in Sintra post, you’ll know that I’m a hardcore fan of George R. R. Martin’s series. Walking in Tallinn’s city walls totally made me feel like I was somewhere in northern Westeros.

Old Town Tallinn, Estonia

Only the best views from the Patkuli Viewing Platform.

Patkuli Viewing Platform

Less than a 10-minute walk away from the NunnaSauna, and Kuldjala defence towers, you’ll find the Patkuli Viewing Platform. You can snap your perfect bird’s-eye view shot of Tallinn’s Old Town then and there.

Viru Gate, Tallinn, Estonia

The Viru Gate. Just look at that seamless integration! 

Old Town Tallinn, Estonia

Another gorgeous cobblestoned side street.

Tallinn Town Hall and Town Hall Square

Tallinn’s Town Hall Square has been the heart of the city for over 500 years. The Town Hall in the centre of the square is around 600 years old.

Tallinn Town Hall Square, Estonia

Check out the Town Hall Square. A [Town Hall] Pharmacy (found in the pale peach building on the left) has operated in the same spot for nearly 600 years.

Just look at that perfectly medieval and grand Town Hall (and picturesque square)!

Old Town Tallinn, Estonia

Obsessed with those splashes of colour. They really pop on rainy days.

Old Town Tallinn, Estonia

Time Travel?! Yup, it's pretty much possible in #Tallinn, #Estonia. Welcome to the Middle Ages: Click To Tweet

Old Hansa, Tallinn, Estonia

Old Town Tallinn, Estonia

Old Town Tallinn, Estonia

Snaps taken along Müürivahe near the Viru Gate. 

Old Town Tallinn, Estonia

The Long Leg Gate Tower in the distance.

St. Catherine’s Passage

Less than a 5-minute walk away from the Town Hall Square, you’ll stumble across St. Catherine’s Passageway. Without a doubt, the passage is one remarkably medieval sight (just look below).

While strolling down this walkway, you are more than welcome to visit the studios and shops of countless artists, such as glassblowers, weavers, and potters.

St. Catherine's Passage, Tallinn, Estonia

The famous passageway. 

St. Catherine’s Passageway and a “Secret” Stone Courtyard (above). Sometimes, unexpected finds are simply the best.

Old Town Tallinn, Estonia

Another shot of the “secret” courtyard.


The Bird’s-Eye View from the top of St. Olaf’s Church

If you want to experience yet another panoramic view of Tallinn’s historic centre, head on over to and up the tower at St. Olaf’s Church.

Old Town Tallinn, Estonia

A snap from the top. 

Check out these 29 photos, and you'll see that the Middle Ages didn't end in #Tallinn, #Estonia: Click To Tweet

The Endless Narrow Side Streets and Passages

I promise you that it’s possible to experience sights reminiscent of Medieval Times around nearly every corner in Tallinn’s Old Town. Knowing that there are so many streets to wander down and explore may feel a little overwhelming at the start. Start off by visiting the specific sites listed above, but make sure to include taking a peek down the side streets – especially those off of the larger streets Lai and Pikk – on your “must do” list too! You won’t be disappointed!

Old Town Tallinn, Estonia

Without a doubt, exploring a well-preserved medieval town is a unique experience. For a fanatic of the Middle Ages like me, exploring Tallinn’s historic centre was beyond memorable. I actually studied history in uni (aside from English Lit.), and I signed up for courses about those wild middle years whenever humanly possible.

FUN FACT: I can read Middle English. (And no, that’s not Shakespearean English. It’s even older)…But the usefulness of knowing Middle English is, again, a whole different story. All I can say is that, so far, it’s either done a good job impressing or terrifying my English students.

All in all, I’m always down for a trip through time back to the Middle Ages. If you have any suggestions about other medieval towns I absolutely must visit, please feel free to share them in the comments section below! 

As always, I’d love to hear your thoughts about Tallinn too!

Happy Travelling


  1. I am a Medieval towns lover so Tallinn is going to be on list now. Also I have never been to Eastern Europe so what a better excuse than this!

    • I am so happy to hear this! Tallinn’s medieval centre seriously took me by surprise in the best way possible. You’ll love it!

  2. Tallinn’s been on my list for absolutely ages! But I’ve been waiting for one of the airlines to run flights from one of my local airports so that I don’t have to travel all the way down to London just for a long weekend! (although also considering combining a visit there with Helsinki). It looks so pretty, colourful, and quaint even in the rain 🙂

  3. Wow… your pictures are stunning! *-* Tallinn must be so beautiful! I’ve been curious about the Baltic states for so long now, I think it’s time that I visit!
    Great post!

  4. We’re thinking about visiting Tallinn next year, so your post was a fascinating read. It really looks so unspoiled, from the City Walls to St Catherine’s Passage. The elk soup sounds intriguing!

  5. This is such a great virtual tour! Love all your photos, it’s definitely brought the place alive. 🙂 I’d love to visit!

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