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.