Top 10 Things to Do in Tallinn: Medieval Walls Meet Digital Innovation
Tallinn is the city that shouldn't make sense. A 13th-century walled old town — complete with Gothic spires, cobblestone alleys, and a pharmacy that's been open since 1422 — exists in the same city that invented Skype, runs 99% of government services online, and has a digital nomad visa called e-Residency.
Medieval and digital. It works. Here's how to experience both.
1. Lose Yourself in the Old Town (Vanalinn)
Tallinn's Old Town is UNESCO-listed and legitimately one of the best-preserved medieval cities in Europe. The cobblestone streets, merchant houses, and Gothic churches date to the 13th-15th centuries. Unlike many European old towns that were bombed and rebuilt, Tallinn's survived WWII largely intact.
Start at Town Hall Square (Raekoja Plats) — the heart of the old town since the 13th century. The Town Hall (1404) is one of the oldest Gothic town halls in Northern Europe. Walk to Raeapteek on the corner — Europe's oldest continuously operating pharmacy (since 1422). They sell medieval remedies (dried snake, mummified hedgehog) alongside modern medicine. Allow 3-4 hours for the full old town.
Pro Tip: Walk the old town at 7AM before the cruise ship crowds arrive. The morning light on the limestone buildings is stunning, and you'll have Raekoja Plats to yourself.
2. Climb Toompea for the Best Views
Toompea Hill is the upper old town — the seat of power since the 13th century. The Estonian Parliament sits in the medieval Toompea Castle. The Alexander Nevsky Cathedral (1900) has five onion domes and Tallinn's largest bells.
But you're here for the viewpoints. Kohtuotsa gives a panoramic sweep of the old town's red rooftops, church spires, and the port beyond. Patkuli viewpoint offers the better angle — terracotta rooftops framed by towers against the Baltic sky.
All free. Allow 1.5 hours. The climb from the lower town takes 5-10 minutes via steep medieval staircases.
Pro Tip: Patkuli at sunset is magical. But go 30 minutes before to secure a spot — word has gotten out.
3. Explore Telliskivi Creative City
A former industrial complex turned into Tallinn's coolest neighborhood. Street art covers concrete walls. Indie shops sell Estonian design. Craft breweries pour local IPAs. Food halls serve everything from Georgian dumplings to Estonian elk burgers.
Peatus is great for local craft beer (pints €4-6). F-Hoone does modern Estonian food in a converted factory with high ceilings and mismatched furniture. Depoo food market has stalls selling everything from ramen to Estonian black bread.
10-minute walk from the old town, north along the railway. Best on weekend afternoons. Free to explore.
Pro Tip: The Saturday market at Telliskivi Flea Market (10AM-3PM) has vintage clothing, vinyl records, and handmade ceramics at prices that make Scandinavian design affordable.
4. Visit the Vasa Museum — Wait, Wrong City. Visit Kadriorg.
Kadriorg Palace & Park was built by Peter the Great in 1718 as a summer residence after Russia conquered Estonia. The Baroque palace now houses the Kadriorg Art Museum (foreign art, 16th-20th century, €8). The park is free, beautiful, and perfect for a morning walk.
The adjacent KUMU — the largest art museum in the Baltics (€12) — is the main event. Estonian art from the 18th century to contemporary. The building itself (designed by Finnish architect Pekka Vapaavuori) is architectural statement. Allow 2-3 hours for both. 15 minutes by tram from center.
Pro Tip: KUMU has free entry on the last Wednesday of every month.
5. Walk the City Walls and Towers
Tallinn's medieval city walls are among the most complete in Europe — 1.9 km of wall and 20 towers survive. Several sections are walkable:
Hellemann Tower and Wall Walk (€4): Walk along a 200m section of the wall between towers with views into the old town and out to the port
Kiek in de Kök (€14 combo with tunnels): A massive 15th-century cannon tower with a museum of Tallinn's history, plus underground tunnel tours (the Bastion Passages — medieval escape routes)
Allow 1-1.5 hours for the wall walk and tower museum.
Pro Tip: The Bastion Passages underground tour is genuinely atmospheric — torch-lit tunnels under the city walls where soldiers moved during sieges.
6. Drink Craft Beer (Seriously Good Craft Beer)
Tallinn's craft beer scene is one of Northern Europe's best-kept secrets. Põhjala Brewery (15 min from center by tram) is the flagship — their Öö (imperial stout) has won international awards. The tap room does tastings and tours.
Koht in the old town is a craft beer bar with 12 rotating taps and knowledgeable staff. Pudel Baar in Kalamaja is the dive-bar version — cheap pints, local bands, no pretension.
Pints run €4-7. In Helsinki (2 hours by ferry), the same beer costs €8-11.
Pro Tip: The Tallinn Craft Beer Weekend festival in June is an excellent excuse to visit.
7. Day Trip to Helsinki by Ferry
Fast ferries cross to Helsinki every 1-2 hours (2 hours, from €15-30 each way). Tallink and Viking Line are the operators. You'll need your passport — Finland is a separate country.
Helsinki is Tallinn's mirror image — more money, more design, less medieval charm. Do it as a day trip, compare prices (everything is 40-60% more expensive in Helsinki), and appreciate what Tallinn offers when you return.
Book online for best prices. Morning departures return in the evening. The ferry has decent restaurants and duty-free.
Pro Tip: The return ferry at sunset gives you views of Tallinn's old town skyline from the water — towers and spires lit golden against the darkening Baltic.
8. Visit the Estonian Open Air Museum
Seventy-two hectares of historic rural buildings — farmsteads, a village school, a wooden church, a fire station — transplanted to a seaside forest at Rocca al Mare. It's an open-air history lesson on how Estonians lived for centuries.
Entry: €10 in summer, €6 in winter. Open daily. Take bus 21 from center (20 min). The Kolu Inn inside the museum serves traditional Estonian food (roast pork, sauerkraut, blood sausage) at reasonable prices. Allow 2-3 hours.
Pro Tip: Visit in late September or October when the forest around the museum turns golden. The autumn colors against the gray Baltic sea are stunning.
9. Eat Estonian at Rataskaevu 16
Rataskaevu 16 is consistently rated Tallinn's best restaurant for traditional Estonian cuisine at fair prices. In a medieval cellar (naturally), they serve wild boar, elk stew, blood sausage with lingonberries, and seasonal game. Mains €14-22. The three-course lunch special (päevapraad) costs about €12.
Book ahead — it's popular with locals and visitors. The building dates to the 15th century. The menu dates to whenever the chef found good ingredients at the morning market.
Pro Tip: Try the elk fillet with juniper berries (about €20). Estonian game meat is underappreciated outside the Baltics.
10. Stand at the Edge of Medieval and Digital
Walk from the old town's 14th-century Viru Gate (the postcard shot — two round towers flanking a cobblestone street) to the e-Estonia Showroom on Lõõtsa 2a in the Ülemiste City district (15 min by tram). This is where Estonia explains its digital society — e-Residency, digital ID, blockchain voting — to visitors and foreign governments.
It's free, by appointment (book online). The contrast between medieval walls and digital governance is the essence of Tallinn.
Alternatively, just notice the WiFi. Free WiFi covers the entire old town. The bus ticket system is contactless. Every café takes cards (many don't accept cash). Estonia doesn't advertise its tech credentials — it just runs on them.
Pro Tip: Download the Bolt app (founded in Tallinn). It's the local Uber equivalent. Airport to old town costs about €8-10.
The Tallinn Summary
Budget: €60-100/day for accommodation, €10-18 for a restaurant meal, €4-6 for craft beer. Tallinn is far cheaper than Helsinki or Stockholm — Nordic quality at Eastern European prices.
Best months: May-September (long days, warm weather, outdoor cafés). December for Christmas markets (Raekoja Plats hosts one of Europe's best).
The Tallinn Card (from €35/24hrs) covers 50+ museum entries, free transport, and walking tours. Worth it if you're visiting 3+ attractions.
Give Tallinn at least 2 nights. The old town is a half-day. Telliskivi, Kadriorg, and the craft beer scene fill another full day. The Helsinki day trip adds a third. And the Open Air Museum is worth the bus ride.
Tallinn isn't trying to be the next Dubrovnik or Prague. It's doing something rarer — being a medieval city that's also the most digitally advanced society on earth, and not making a fuss about either.
For full planning details, our complete Tallinn travel guide covers where to stay, what to eat, and budget tips. For a personal take, our weekend narrative captures the atmosphere. If you love medieval walled cities, Bruges and Kotor offer the same charm.
