A CITY THAT WENT TOO FAR IN CATERING TO TOURISTS

For no real reason, I was stupidly excited about going to Tallinn. That was a mistake because when the city didn’t reach my high expectations, it left the city feeling a little lackluster. That doesn’t mean I don’t think Tallinn is worth going to - but I will say that you shouldn’t go with expectations that are too high.

Tallinn is most famous among tourists for having one of the best preserved medieval cities in Europe. For modern reasons, Tallinn is also a well-known tech hub and is a center of entrepreneurism in Europe. I think it’s the latter that really shines on a visit, though. While it is true that Tallinn’s Old Town is a well preserved historical center, the district has so thoroughly caved to tourism that there is little local charm or economy left. It feels a bit like an amusement park or a singular attraction - a place you go to see but not to have a holistic experience of another place. Once you leave the Old Town, though, the modern spirit of Tallinn shines through quickly. You begin to see the locals, who seem cool and bit edgy, in a modern city.

SPEND A FEW HOURS WANDERING THROUGH OLD TOWN AND TOOMPEA HILL

If you’re going to Tallinn for your first time, I think you do have to go to the Old Town - which is divided into the Lower Town (where most of the medieval sections are) and Upper Town (which has always been the seat of power in Estonia).

The Lower Town feels a bit like the other old towns in the Baltics - but taller and more stately. One of the main draws is the preserved fortifications - the city wall, the Viru Gate, and the towers (Fat Margaret and Klek in de Kok). You’ll also want to go to Town Hall Square (Raekoja plats), wander around aimlessly, and I recommend going to St. Catherine’s Passage. To fend off disappoint, go in expecting to enjoy a charming medieval feel - but not to expect any single piece of architecture to be awe-inspiring.

In Upper Town, you’ll find Toompea Castle - which was originally a Swedish fortification and is now the seat of the Estonian Parliament. You can also go to Alexander Nevsky Cathedral across the street which is very different architecturally from Tallinn generally.

The whole of Old Town should only take a few hours to explore. It’s not the kind of charming local economy you could get lost in for days; most of the business are designed to cater to tourists. I’d plan to see all of the buildings and then head out into the city to eat with the locals.

EXPLORE MODERN TALLINN

Once you’ve finished Old Town, I’d recommend heading east to the Saldana neighborhood near Rost Bakery (where you’ll inevitably find a line for their cinnamon buns). The area is charming architecturally and you’ll find it busy with locals eating at the locals cafes and restaurants.

From there you can head south wandering around the outskirts of Old Town to find a thoroughly modern city that feels more like the United States or Australia than Europe. It’s here you will bump into the spirit of Tallinn - which feels lively and energized.

HEAD TO KADRIORU PARK

A couple of kilometers away from Old Town, you’ll find a large park with the former palace of Peter the Great - Karioru Palace - along with its grounds and gardens. Nowadays, the park houses an art museum and presidential residence. Unfortunately, I ran out of time and didn’t get to go - but it does look beautiful.