Tallinn is a city that feels like stepping into a fairytale, where medieval towers stand proudly against a backdrop of modern life. My trip to Estonia’s capital was a beautiful blend of history, art, and some unexpected surprises. Among these surprises is the city’s emergence as a vibrant hub attracting young international talent, particularly in the tech sector. With its high level of English proficiency and a thriving startup culture, Tallinn has become an appealing destination for young professionals seeking innovative opportunities. I met a young American man while traveling in Tbilisi, Georgia, who moved to Tallinn a few years ago to work at a tech company. During my tours, the guides shared insights about the city’s dynamic environment, which boasts over 1,000 startups and is home to notable companies like TransferWise, Bolt, and Pipedrive.
My first stop was the Alexander Nevsky Cathedral, a striking Russian Orthodox cathedral perched atop Toompea Hill. Its onion domes gleamed in the sunlight, and stepping inside, I found myself enveloped by the soft glow of candles and the rich scent of incense. It’s a peaceful place, despite the bustling crowds outside, and I took a moment to soak in the serenity before heading out to explore the rest of the Old Town.
Alexander Nevsky Cathedral
Wandering through the winding streets, I made my way to Tallinn Town Hall. This medieval gem dominates the Town Hall Square, a lively meeting point for both locals and tourists. I decided to climb the Town Hall Tower—an adventure in itself, with narrow stone steps spiraling upward. The panoramic views at the top made every step worth it, offering a breathtaking sweep of red rooftops and the Baltic Sea shimmering in the distance.
Not far from there, I stumbled upon St. Nicholas’ Church, where the famed "Dance of Death" painting draws visitors from around the world. What surprised me most about this historic church was the modern convenience of an elevator—a rare find in old European buildings, and a welcome break from all the stair climbing! It was an odd but delightful mix of old and new, much like Tallinn itself.
Next on my journey was the Tallinn Museum of Orders of Knighthood, a fascinating little museum showcasing intricate medals and the storied history of chivalry. Though small, it packed a punch with its detailed exhibits. Afterward, I visited St. Mary’s Cathedral and climbed yet another tower (I can’t resist a good city view), enjoying the peaceful atmosphere of the church and its beautiful gothic architecture.
A highlight of my trip was the Vabamu Museum of Occupations and Freedom, which takes you deep into Estonia’s turbulent past under Soviet and Nazi occupations. The interactive exhibits brought history to life, making the struggles of the Estonian people tangible in a way that hit me deeply. I left with a new understanding of the resilience and strength of this small nation.
Vabamu Museum of Occupations and Freedom
Soviet sparkling water machine. The water was really good!
Just outside the city, I ventured to the Estonian Open Air Museum, a sprawling showcase of traditional Estonian life. Walking through old farmhouses and windmills, surrounded by lush green fields, I felt like I had stepped back in time. One of the highlights was the 1960s farmers' cooperative house, which featured apartments decorated to reflect the distinct styles of the 60s, 70s, 80s, and 90s. The 90s apartment was especially nostalgic—it even smelled like the 90s, transporting me back to my childhood with its distinct blend of scents. Adding to the immersive experience, there were people dressed in period costumes who demonstrated traditional crafts, explaining how they made fabrics and other essential items. This interactive element brought the past to life, allowing me to appreciate the skills and artistry that shaped Estonian heritage. This quiet, reflective escape from the hustle of the city offered a beautiful way to see a different side of Estonia.
Estonian Open Air Museum
Back in the Old Town, I visited the Estonian Museum of Applied Art and Design, a must for anyone who loves exploring local creativity. From textiles to ceramics, the exhibits were a testament to Estonia’s innovative spirit. And then there was the Kiek in de Kök Museum, where I delved into Tallinn’s medieval defenses, followed by an eerie walk through the underground bastion passages that featured the different types of people who lived there such as the punks of the 80s.
After emerging from the depths of Tallinn’s medieval past, I found myself drawn to a more unconventional attraction—the Banned Book Museum. Tucked away in a quiet corner of the city, this small yet thought-provoking museum sheds light on literary works that have faced censorship throughout history. It’s free to enter, though donations are welcomed to support its important mission. From Mein Kampf to The Green Book, the museum showcases a wide range of banned books, complete with detailed information on where and why each was banned. I was even surprised to find that Barack Obama’s memoir, The Audacity of Hope, had been banned in Florida.
Required reading in Libya during Gaddafi's rule. At the Banned Book Museum.
The Estonian Maritime Museum, a captivating tribute to Estonia’s deep connection with the sea. Housed in the historic Seaplane Harbour, the museum is an immersive experience that appeals to both kids and adults alike, offering interactive exhibits and a fascinating journey through Estonia’s maritime history, from ancient Viking trade routes to modern naval innovations. I explored displays featuring everything from sea mines to hands-on sections about water safety, perfect for younger visitors. The highlight for me was stepping inside the World War II-era submarine, Lembit. Behind the museum, a beautifully restored steam-powered icebreaker ship called Suur Tõll awaits visitors. Free to enter with a museum ticket, this massive ship, which played a vital role in keeping trade routes open in icy conditions, offers an exciting glimpse into Estonia’s maritime resilience, making the museum a must-visit for all ages.
Me inside the WWII era submarine and wearing the Full Coverage Tank
Tallinn’s Old Town is filled with shops selling "Estonian amber" jewelry, which initially piqued my curiosity. However, after seeing amber sold only in the tourist areas and noticing its conspicuous absence elsewhere, I became a little suspicious. When I mentioned it to my American friend who lives in Tallinn, my doubts were confirmed—Estonian amber is mostly a scam. Even my tour guide scoffed when someone asked about Estonian amber. The majority of authentic Baltic amber comes from Latvia and Lithuania, not Estonia. If you’re looking to buy amber, it’s worth knowing this before you spend money on something that isn’t genuinely local, overpriced, and rumored to be fake.
Of course, no trip would be complete without indulging in Tallinn’s diverse culinary scene. My favorite spot was Rataskaevu Restoran, a cozy, bustling place where I had the best Estonian meal of the trip. I quickly learned that reservations are essential here—every table was full, and walk-ins were politely turned away. For dessert, I couldn’t resist stopping by Karu Talu Šokolaad to pick up some of their amazing cookies. It's up there with Levain's Bakery in NYC. Another hidden gem was Viktus Kohvik, just outside the city center, where the prices were friendlier but the food just as delicious.
One evening, I met my American friend who lives in Tallinn for dinner and then we went to the Depeche Mode Bar (a few doors down from the cookie place), a quirky shrine to the band. Even if you’re not a fan, it’s worth checking out for its unique atmosphere. My friend, an American who I met in China and now lives in the Pacific islands, told me about the Depeche Mode Bar when I messaged her about traveling to Tallinn. It's a small world. For a rooftop treat, Maiasmokk Kohvik offered views of both the Old Town and the Russian Embassy across the street—an odd juxtaposition, but fascinating nonetheless.
Though I had planned to visit Peter the Great House, Kadriorg Art Museum, and the highly recommended Kumu Art Museum, I was disappointed to find them closed on Mondays—note to future travelers, plan accordingly! Instead, I wandered around a nearby park and then took an Uber to the Memorial to the Victims of Communism and then walked to the Soviet Statue Graveyard, a somewhat eerie space filled with statues from Estonia’s Soviet past. The Soviet statue graveyard in Tallinn is smaller than the one in Budapest and lacks the Soviet music playing in the background, but it's free and offers detailed descriptions and photos of where each statue was originally placed, adding valuable context to their history. Both sites were a sobering reminder of the country’s complicated history.
Statues of Lenin and Stalin at the Soviet Statue Graveyard
One unexpected find was the Jewish Community of Estonia Museum, a small but important museum tucked away in the city. Prebooking is essential, either by phone or email, because all guests are given a free tour, though donations are welcome. During my visit, I learned about the tragic history of the Jewish population in Estonia. Before World War II, there weren’t many Jews in the country, as they were largely forced to live in the Pale of Settlement of the Russian Empire, which included the ghettos of Belarus, Lithuania, Moldova, Ukraine, Poland, Latvia, and Russia. However, Jews who fought for the Russian Empire were permitted to settle in Estonia. By the time the Nazis took over in 1941, only about eight Jews remained, as the Nazis declared Estonia Judenfrei (Jewish free). The synagogues that once stood in the city were destroyed by both the Nazis and the Soviets, but a new synagogue has recently been built next to the museum. A tour of the synagogue is also available, providing a poignant reminder of the resilience and history of the Jewish community in Estonia.
On my last full day in Tallinn I visited Balti Jaama Turg, a bustling market where you can find everything from fresh produce to antiques. A word of caution—there’s a section selling Nazi memorabilia, which was both surprising and unsettling. Several countries, particularly in Europe, have enacted laws that ban the sale and display of Nazi memorabilia, aiming to prevent the glorification of hate symbols linked to the atrocities of World War II. Despite that, the market had a vibrant energy and was a great place to mingle with locals. I was warned to avoid the food there, because it's average and overpriced.
One of the last things that I did was visit the Russian neighborhood of Kalamaja, which was a fascinating journey into a unique cultural landscape marked by old Soviet-era apartment buildings and the sounds of Russian spoken on the buses. During many of my tours, the tour guides hinted at the underlying friction between the Russian-speaking population and the Estonian-speaking residents, a tension rooted in Estonia's complex history with Russia. Russians have been part of Estonia since the Soviet era, and their presence remains significant today. One of my tour guides, whose mother is Russian-speaking, shared that she was cursed at simply for looking Russian, highlighting the societal challenges that persist. Her mother had even hidden her Russian background for years, navigating a delicate balance between identity and acceptance. There are efforts to incorporate the Russian-speaking population into the greater Estonian economy, but this has been difficult because many Russian-speaking Estonians only speak Russian.
As I walked back to my accommodation in the Kalamaja district, with its colorful wooden houses and hipster cafes, I reflected on the city. Tallinn is a place where history and modernity collide in the most fascinating ways. From its medieval streets to its cutting-edge art scene, every corner holds a story. I left with a sense of wonder and a strong desire to return, knowing there’s still so much more to explore.