Estonia had never been at the top of my travel wish list, but when I was living in Stockholm in 2018, I knew I had to take advantage of its proximity. My best friend Solomon had come to visit me in Sweden, and Tallinn enticed us as an ideal weekend getaway.
Part of its allure was how off the beaten path it sounded at the time. Hardly anyone I knew had been to Tallinn, and my thought process was pretty much along the lines of, "Well, why the hell wouldn't I visit Estonia?"
We arrived in Tallinn with absolutely zero expectations, but we left completely blown away.
Everything about Tallinn pleasantly surprised me. First and foremost, Tallinn's medieval old town defines storybook charm. It reminded me of the fairytale scenes of Prague, but smaller and without the crowds.
We were staying in an apartment just a short walk away from old town (where the monochrome Soviet-style architecture seemed stark and slightly oppressive). On our first day in Tallinn, a kaleidoscope of colors greeted us upon wandering up to the old town. I simply couldn't cease stuffing my eyes with its excessively picturesque streetscapes.
Though my favorite activity in old town Tallinn was aimlessly wandering, there were still plenty of things we wanted to see. (And eat. And drink. And eat some more. All of which are pretty on-brand over here.)
Aside from drinking Aperol Spritzes in charming plazas, some highlights included the Museum of Medieval Torture (which is exactly what it sounds like) and the KGB Prison Cells, a bleak basement in the heart of an otherwise cheerful old town, painting a hauntingly realistic picture of much darker times (and many, many human rights violations).
Some less grim sights included St. Catherine's Passage, a medieval street that feels like stepping back in time, and the striking Alexander Nevsky Church commanding the city atop Toompea, in which we may or may not have accidentally walked into a funeral.
Along with getting up close and personal with Tallinn's striking details, such as its colorful homes, churches, and array of ornate doors, there's also no shortage of sites to soak in the city's sublime vistas.
They say the best views come after the hardest climbs, and while getting to the top of St. Olav's Church was only about 232 steps, it was still steep and slippery enough for me to fear for my life. To avoid crowds in the acutely narrow spiral staircase, go right when it opens at 10:00 am.
The Kohtuotsa viewing platform was less crowded (and less risky), and still boasted panoramas of Tallinn's sea of pastel buildings with cherry red rooftops.
At the time, I couldn't help but wonder if in 5-10 years this will be another "it" destination, but in that moment it felt seemingly undiscovered... except for the cruise ship passengers during the day, leaving it completely deserted at night. As a disclaimer though, we visited during the off season, so I imagine the crowds do get worse in peak cruising times. (It's always those damn cruises, am I right?)
Views from St. Olav's Church
Alexander Nevsky Cathedral
What surprised me the most was how Tallinn was an unexpected gastronomic haven. The culinary scene here is thriving, and for the most part it's all pretty affordable. Both Celiacs, Solomon and I found fantastic options for gluten free dishes that far exceeded our expectations.
Of all the phenomenal restaurants we visited, Rataskaevu 16 topped the list. Every dish was impeccably prepared and served by the most friendly staff. It was arguably the best meal I had in all of 2018, and inarguably one of my favorite experiences in Tallinn. (Reservations recommended.)
Slow roasted pork belly with vegan quince from Rataskaevu 16
Oven baked goat cheese with vegetables, raspberries, and vanilla cream
Rataskaevu 16
Duck leg confit and ostrich carpaccio from DOM (since closed). A true gastronomic experience.
Von Krahli Aed
For those with food allergies or intolerances (both of the physiological and moral variety), Vegan Inspiratsioon is a convenient go-to breakfast spot. To fuel up for the day, we'd feast on gluten free peanut butter pancakes, raw cakes or pastries, and plenty of almond milk lattes.
The Balti Jaam Market between old town and Telliskivi (the "creative city") has something for everyone, including local goods, fresh produce, live music, and trendy pop ups specializing in everything from home cooked Ukrainian food to Instagrammable bakeries.
Not only was the food itself fantastic (their menu has surely changed since my visit, but I had a memorable dinner of pork ribs and a prosciutto salad with sun-dried tomatoes and a coconut mango dressing), but also the ambiance was as hip and eclectic as the neighborhood itself.
A brunch of rösti, fried ricotta balls, and mimosas (of course)
Telliskivi, or the "creative city", is a former industrial complex with old railway buildings, studios, bars, shops, street art, and modern art installations. A true haven for hipsters, be prepared for lots of photo opps and damn good food.
There is also a flea market on Saturdays with antiques, weapons, and USSR relics. Somehow I ended up wandering into a vast, dark hangar full of antiques, which felt like a slightly ominous time warp. Amidst the busted stuff, I found some unique mementos of former Soviet decay. (Certainly not your average souvenirs.)
A true jewel of the Baltics, Tallinn was a surprising feast for the senses. Spending a long weekend here was a definite highlight of my stint in Scandinavia. Visit Tallinn and prepared to be charmed.
