A Long Weekend in Tallinn: Spires, Startups, and the Baltic in Between
I don't know what I expected from Tallinn. I had vague impressions: medieval walls, cheap beer, Skype's birthplace. Three days later, I had a sharper picture. Tallinn is the place where a 15th-century pharmacy sells dried hedgehog next to ibuprofen, where the government is more digital than most Silicon Valley startups, and where a pint of world-class craft beer costs less than a cup of coffee in Stockholm.
Here's how it went.
Day 1: Into the Walls
Flew in from London. Tallinn Airport is tiny — one terminal, one runway. Tram #4 from the airport to the old town: 10 minutes, €2. I was walking on cobblestones by 2PM.
The old town hits you immediately. The Viru Gate — two round medieval towers flanking a narrow street — is the Instagram shot. Beyond it, the streets tangle into a maze of Gothic buildings, church spires, and alleyways too narrow for cars. The buildings are limestone and painted plaster, mostly three or four stories, with details that reward looking up: carved doorframes, iron brackets, guild signs.
Town Hall Square (Raekoja Plats) is the center. The Gothic Town Hall (1404) is one of the oldest in Northern Europe. I walked into Raeapteek — Europe's oldest operating pharmacy. The front room sells normal medicine. The back room has a display of medieval remedies: dried snake, mummified hedgehog, a bottle of something labeled in Latin that I didn't want to investigate further.
Walked up to Toompea Hill via the medieval staircase off Pikk Jalg (Long Leg) street. The Alexander Nevsky Cathedral's five onion domes look Russian because they are — built in 1900 when Estonia was part of the Russian Empire. Inside: gold icons, incense, a handful of worshippers crossing themselves.
The Kohtuotsa viewpoint stopped me. The entire lower old town spread below — terracotta rooftops, the spire of St. Olav's Church (once the tallest building in the world at 159m), the port, and the Gulf of Finland stretching flat and grey to the horizon.
Dinner at Rataskaevu 16 — a medieval cellar restaurant that serves Estonian food without the gimmick. I ordered elk fillet with juniper berries (€20). The meat was lean, gamey, tender. The black bread on the side was dense enough to build a house with. Estonian food is honest. It doesn't try to impress. It just feeds you.
Day 2: Beyond the Walls
Morning in Kalamaja — a neighborhood north of the old town that was once a fishing village and is now Tallinn's equivalent of Brooklyn or Shoreditch. Wooden houses painted in pastel colors. A café (Kohvik Røst) where the barista had opinions about water temperature. A vintage shop where I found a Soviet-era leather satchel for €15.
Then Telliskivi Creative City. A former railway factory complex. Street art on every concrete wall. An indoor food market (Depoo) where I ate Georgian khinkali (dumplings, 5 for €4) at a counter next to a woman from Tbilisi who told me her recipe was better than her grandmother's.
Põhjala Brewery — 15 minutes from the center by tram. The tap room pours their entire range. I tried Öö (imperial stout, 10.5% ABV, €6 for 330ml). It tasted like dark chocolate and coffee and regret (the good kind). The IPA (Virmalised, €5) was crisp and bitter. Tallinn's craft beer scene is genuinely underrated.
Afternoon at KUMU — the Baltic's largest art museum in Kadriorg park. The permanent collection tracks Estonian art from the 18th century through Soviet occupation to independence. The Soviet-era art is fascinating — officially "socialist realism" but often subtly subversive. The museum building (all sharp angles and glass) is a work of art itself. Entry €12.
Evening: the old town after dark. The cruise ship passengers were back on their boats. The streets were quiet. I walked Raekoja Plats alone. The Town Hall was lit from below. A cat crossed the square. A man was playing accordion somewhere I couldn't see.
Day 3: Water and Departure
Morning at the Estonian Open Air Museum at Rocca al Mare. Bus 21, 20 minutes. Seventy-two hectares of rural Estonian buildings — farmsteads, a windmill, a village school, a wooden church — relocated from across the country and reassembled in a seaside forest.
The place is enormous and empty on a Thursday morning. I walked through a 19th-century farmstead where a woman in period dress was demonstrating how to make Estonian black bread. The process takes two days. The bread lasts a week. Estonia's culinary heritage is built on patience and preservation.
Lunch at the Kolu Inn inside the museum — roast pork with sauerkraut and potatoes. €11. Traditional, filling, unpretentious.
Walked the coastal path back toward the city. The Gulf of Finland was slate grey. A ferry to Helsinki crossed the horizon. The wind smelled like salt and pine.
Final stop: Pudel Baar in Kalamaja. A dive bar in a warehouse. Punk rock on the speakers. A pint of local lager for €3.50. A bartender with a tattoo of the Tallinn skyline on her forearm who told me Tallinn was "the best city in Europe that nobody visits."
I'm inclined to agree.
Would I Go Back?
Absolutely. And I'd add a fourth day for the Helsinki ferry trip (2 hours each way, from €15). The contrast — Helsinki's polished Nordic design against Tallinn's raw medieval-digital hybrid — would sharpen both cities.
Tallinn is cheap (€10-18 for a restaurant meal), compact (the old town is walkable in 30 minutes), and genuinely interesting in a way that doesn't rely on one big attraction. There's no Eiffel Tower. No Colosseum. Instead, there's a medieval walled city where you pay for beer with your phone, where the WiFi is free on every cobblestone street, and where a craft brewery makes stout that could compete with anything from Portland or London.
The Tallinn Card (from €35/24hrs) covers museums, transport, and walking tours. Bolt (born here) handles taxis. The airport is 10 minutes from the old town.
Pack warm layers — even in summer, the Baltic wind has teeth. In winter, pack everything. The cobblestones are beautiful. They're also ice rinks from November to March.
Tallinn. Medieval walls, digital soul, €4 craft beer. I don't know what else you need.
For the practical breakdown, our complete Tallinn travel guide covers everything. Our top 10 list helps prioritize what to see. If Tallinn's value-for-money medieval charm appeals to you, Krakow offers a similar combination at Central European prices.
