Tallinn, Estonia: A Truly Medieval City
- Skye McKenzie
- Apr 9
- 3 min read
We started our second day in Helsinki with an early wake-up—6am, ready to head out the door by 6:30. Destination: Estonia!
The Ferry Trip
Despite the ticket saying to arrive two hours before departure, the terminal was eerily quiet when we showed up a bit late. Clearly, that advice is for tourists who haven’t quite figured things out yet—like me! We grabbed a coffee and warmed up from the brisk -2°C walk, grateful for a bit of heat.
The ferry experience was… interesting. The Eckerö line boat—picture a floating 1970s Vegas with a karaoke bar being set up and Bingo just getting underway. We gave both a miss and found a sunny nook in the café for a light bite and a power nap (well, for Jase anyway). Two hours across the Gulf of Finland, we were ready to disembark.
Hello, Tallinn
When we arrived in Tallinn, the air somehow felt even crisper. We wandered for a bit before finding a café said to be the “best in Tallinn”. While it was charming—nestled in the old town and clearly steeped in history—I’m not sure it lived up to the hype. Still, the quiche and salad made for a delicious, light lunch before we ducked into a souvenir shop and then met up with our guide, Max.
A Walking Tour of the Old Town
Max was fantastic. A young Estonian linguist with Russian heritage, he encouraged us to ask anything. He began by walking us through Estonia’s complicated political history—bounced between the hands of Germany, Sweden, Russia, and more. Estonia has only been independent since 1991 (this time), emerging from the grip of the Soviet Union. It’s been through a lot. Of course, the modern Tallinn is a truly cutting edge digital city—home to Skype and Bolt, amongst others. But that wasn’t what we were here to see.
We began our tour in Vanalinn, Tallinn’s old lower town. The town hall, while under restoration, still showcased its fierce dragon sculptures dating back to 1629. We moved on to St. Nicholas’ Church—now a museum rather than a place of worship. Originally built in the 1200s, it was heavily damaged by a Soviet air raid during WWII and rebuilt since.
Nearby, in a small park, Max pointed out a curious sight: an old truck parked since 1992. It sits on a tiny parcel of land that seems to be privately owned, yet is technically government property. A decades-long standoff continues.
Next was the War of Independence Victory Column, erected in 2007 to commemorate Estonia’s 1918 independence from Russia. From there, we saw the Kiek in de Kök tower—its name hilariously translating to “peek into the kitchen.” Something to do with cannons and fire sources, but honestly, I was just taken by the name!
Crossing into the upper town, we visited the Parliament building and learned about Estonia’s single-house republican system. With nine political parties—seven with actual influence—coalitions are the norm rather than the exception.
Right across the street stood the Alexander Nevsky Cathedral, part of the Moscow Orthodox Church, built in the 1800s. Then came St. Mary’s Cathedral—the oldest church in Tallinn with, amusingly, the newest spire. We wrapped up the tour with a stroll to two excellent viewpoints over the city and a walk along a street wedged between the walls of the lower and upper towns. So medieval. So cool.
Back to Helsinki
By this point, the cold had truly set in, so we made our way back to the port where our Viking Line ferry was waiting. Different line, but the same strange, glitzy, floating Vegas vibe. We grabbed a bite to eat on board to save a late night. I rate food on the boat 5/10 stars.
It was a long day of travel, but totally worth it—Tallinn’s old town was a fascinating and beautiful detour. One for the memory books.
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