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Tallinn, capital of Estonia, is, quite simply, enchanting. Exploring the best-preserved medieval city in Northern Europe is like stepping into a fairytale as you stroll along cobbled alleys, gazing up at graceful Gothic spires and pointed turrets and admiring half-timbered houses with candy-colored facades.

The original city, which is remarkably intact, dates back to the 13th century, although there’s been a fortress here since 1050. Over time, Tallinn has been settled by wealthy seafaring families from Germany, Denmark, Russia, and Sweden, and for the 48 years prior to 1991, was under Soviet rule.

Now a UNESCO World Heritage Site, Tallinn has many faces: the impossibly photogenic Old Town; a thriving tech and food culture; and the brutalist-style architecture that’s a legacy of the Soviet years. You could spend days unpeeling the layers of history. Here are some of the best things to do in Tallinn.

Lose Yourself in the Old Town

Medieval buildings in Old Town Tallinn

Old Town

The Old Town, or Vanalinn in Estonian, is crammed with ancient, crooked buildings, many of which retain their original medieval names. Wander into the narrow lanes like St. Catherine’s Passage, and you’ll come across medieval marvels like old monasteries, merchants’ houses, craftsmen’s guilds, and cobbled squares, polished smooth over the centuries. Tallinn was once encircled by walls, and even these are remarkably well preserved, with large stretches intact and as high as 45 feet in some places.

Raekoja Plats, or Town Hall Square, forms the heart of Vanalinn. For centuries, it’s been the hub of city life, dominated by the magnificent Gothic Town Hall, which now contains a medieval museum. You can climb to the top of the Town Hall’s tower as high as the weathervane, which is the emblem of the city. In midsummer, when there are as many as 18 hours of daylight, the square buzzes with outdoor bars and cafés, buskers, and market stalls late into the long, sunlit evenings.

Potions at an old pharmacy called Raeapteek


Take a moment to peek into the Raeapteek, the oldest continuously operating pharmacy in Europe and once the personal pharmacy to the Russian tsars. Today, the Raepteek is like stepping through a time warp into a setting of polished wooden cabinets, bottles of mysterious colored liquid, and a small, dusty display of historical medicinal implements and potions. It’s one of the most fascinating things to do in Tallinn.

Marvel at Marzipan Art

Café-museum Maiasmokk amid cobbled streets

Café Maiasmokk

Ready for a coffee break? Drop into Café Maiasmokk, the oldest in Estonia, its high-ceilinged interior reminiscent of a grand, 19th-century coffee house. Tallinn has a thriving coffee culture, and at Maiasmokk, you will struggle to resist the decadent chocolate pavlova, almond croissants, and cherry truffles.

There’s a small marzipan museum in the café, and you can watch intricate marzipan fancies being decorated while you sip your cappuccino. Estonia claims to have invented marzipan, originally (and somewhat dubiously, for medicinal purposes; at one point, it was dispensed from the Raeapteek pharmacy.

Dance With Death in St. Nicholas Church

Things to do in Tallinn - St. Nicholas Church

St. Nicholas Church

Another gem of the Old Town is St. Nicholas, a church that was all but destroyed in World War II by Soviet bombs and later, fire, but rebuilt, its Gothic splendor painstakingly restored. Now, it’s deconsecrated and serves as the Niguliste Museum to house the 15th-century religious art treasures that were saved from the bombing.

The eerie, 23-foot canvas of Bernt Notke’s Danse Macabre is magnificent, all the more so when you remember that it’s just a fragment of the original, which was nearly 100 feet wide. If you’re here on a weekend, try to attend one of the hauntingly beautiful organ recitals; St. Nicholas is famous for its wonderful acoustics.

Gaze Over the Rooftops From Toompea

Things to do in Tallinn - Toompea

Toompea Castle

The gentry of Toompea, the upper section of the Old Town, would look down, literally, on the people of Vanalinn. This former stronghold gazes out over the tangle of medieval streets below, with magnificent views. At the heart of Toompea is the elaborate, rose-pink Toompea Castle, built in the 18th century and now home to the Estonian Parliament, and opposite, the magnificent, onion-domed Alexander Nevsky Cathedral.

This grand Russian Orthodox structure, built in 1900 when Estonia was still part of the Czarist empire, is rich inside with mosaics and icons, the scent of incense heavy in the air. The bell towers house 11 bells, the largest of which weighs a massive 15 tons, all brought from St. Petersburg. Arrive just before a service, and you’ll hear the magical melodies of the bells pealing.

Snap the Perfect Instagram Shot

Beautiful landscape from Kohtuotsa viewing platform

Kohtuotsa viewing platform

Tallinn is dotted with lookouts and viewing platforms—understandably, the locals want to show off their gorgeous city—but the most famous spot is Toompea Hill’s Kohtuotsa viewing platform. Here, you’ll get that iconic shot down over the russet rooftops and church towers, all the way to the Gulf of Finland. A simple graffito painted on the pink wall, “The Times We Had”, forms a thought-provoking backdrop to many a portrait.

Climb Fat Margaret

Historic tower of Fat Margaret

Fat Margaret

Some 26 of Tallinn’s original 45 stone defensive towers remain. Two of the most impressive are the chunky Coastal Gate and Fat Margaret, a former prison and gunpowder store at the top of Pikk Street, the main thoroughfare of the Old Town.

Nobody knows where the name came from. Some believe Fat Margaret was a particularly large cannon, while others say the tower is named after a portly cook who used to work here, feeding visiting sailors.

Inside Fat Margaret, there’s a branch of the Estonian Maritime Museum spanning four floors and covering everything from Neolithic fishing gear to a 700-year-old wreck, the Koge. Visiting is one of the top things to do in Tallinn for nautical enthusiasts. Head up to the top for more great views over the harbor and Old Town.

Go Underground at Kiek-in-de-Kök

Cannon tower of Kiek-in-de-Kök

Kiek in de Kök

A 15-minute stroll through the Old Town from Fat Margaret will lead you to another cannon tower, the hulking, 15th-century Kiek in de Kök, built by the Swedes but used as a bomb shelter during World War II. The name actually means “peek into the kitchen,” as you could allegedly see into the kitchens of the grander houses of the lower town from the top floor of the tower.

The upper floors today house a collection of military paraphernalia, although in a way, the nine massive cannonballs embedded in the outside, fired by the army of Ivan the Terrible in the 16th century, are the most evocative aspect of the tower. Kiek in de Kök also conceals the entrance to a warren of mysterious 17th-century bastion tunnels, which you can visit on a guided tour.

Hang Out in Hipster Kalamaja

Colorful neighborhood of Kalamaja


A visit to the boho district of Kalamaja is one of the best things to do in Tallinn beyond the Old Town. This is a great spot for strolling, grazing, and shopping along streets lined with colorful wooden houses. Stop by Balti Jaama Turg, a covered, two-story food hall crammed with stalls selling anything from sushi to bao buns, cheeses, wild boar sausages, hand-made chocolate truffles, and fresh berries. There’s bric-a-brac here, too—it’s the perfect place to pick up vintage gear and ironic Soviet-era trinkets.

You’ll find designer stores at hipster Telliskivi Creative City, a complex of recycled warehouses adorned with spectacular street art and housing some of Estonia’s most successful tech startups, as well as some cool galleries, not least Fotografiska, the Swedish Museum of Photography.

Also worth a couple of hours in this area is the Lennusadam Seaplane Harbour, part of the Estonian Maritime Museum, housed in a Russian-built aircraft hangar. The centerpiece of the museum is the Lembit, a completely intact 1930s submarine built by the British. You can also explore a 16th-century wreck and a Finnish icebreaker.

Admire Art in Kadriorg Palace

Red and white exterior of Kadriorg Palace with garden

Kadriorg Palace

To the east of the city, the opulent Kadriorg Palace sits at the heart of Kadriorg Park, Estonia’s answer to Versailles, filled with manicured lawns, formal flower gardens, splashing fountains, and tree-lined alleys. The park and the striking, red-and-white summer palace were developed by Peter the Great in the 18th century, and both are named for his wife, Catherine I. Take time to step inside the Baroque palace to admire both the extravagant interiors and the art collection, part of Estonia’s national museum, featuring European and Russian art from the 16th to the 20th centuries.

There’s a bigger collection, also in Kadriorg Park, at futuristic, award-winning Kumu Art Museum, its glass-and-stone exterior a stark contrast to the frilly confection of the palace. Inside, you’ll find a permanent collection of Estonian pieces ranging from surrealism to pop art, and changing exhibitions of international and contemporary work.

Vast amphitheater of Song Festival Grounds

Song Festival Grounds

If you wander even further, you will arrive at the Tallinn Song Festival Grounds, an unimaginably vast amphitheater that’s home to the Estonian Song and Dance Celebration, which brings together up to 15,000 performers and 75,000 spectators every five years.

Hike Woodland Trails in Nõmme

Woodland trail In Nõmme


If you’re wondering what to do in Tallinn on one of those uncharacteristically hot summer days, head for the cool of the pine forest. You’ll see a quieter face of the city in the sleepy quarter of Nõmme, a pine-shaded summer retreat favored by locals in the 19th century.

You’ll find colorful clapboard houses, cozy cafes, and grander, art-nouveau residences lining the leafy streets, as well as a vibrant market packed with Estonian produce, from forest berries to hand-picked mushrooms, local honey, and meat products. There are walking and cycling trails under the pine trees, too. On a hot day, Nõmme is a lovely escape from town, and an easy 15-minute train or taxi journey from the center.

Sample Local Spirits at Liviko Distillery

Food and drink play an important role in Tallinn’s culture, and no visit is complete without an insight into how the local specialties are produced. The Liviko Distillery dates back 120 years and makes gin, rum, and vodka, among other concoctions.

There’s an interactive museum, a tour of the historic factory to see the copper stills and the array of botanicals used in productions and, of course, a chance to taste the products, which include Crafter’s Gin, Viru Valge vodka, Caribba rum, and Vana Tallinn, a uniquely Estonian liqueur.

Experience Village Life at the Viimsi Open Air Museum

Things to do in Tallinn - Viimsi Open Air Museum

Viimsi Open Air Museum

Step back in time at this fascinating museum and see what life in an Estonian coastal village was like in the 1820s. The village has been cleverly preserved, and you’ll see fishing net sheds, boat hoists, and racks for drying the fish, as well as a smugglers’ cellar.

There are two fishermen’s houses, the larger of which complete with barn. If you’re traveling with kids, they’ll enjoy hanging out with the farm animals. A farmers’ market takes place every Saturday, selling authentic Estonian produce. Historical interest aside, the coast at Viimsi is lovely, green fields sloping down to the stony beaches of the Baltic Sea, the skyline of Tallinn in the distance.

Take a Trip Through the Soviet Era

Old jail KGB Prison Cells

KGB Prison Cells

Soviet heritage is just one of Tallinn’s many faces. Pack a sense of humor if you join one of the Soviet-era tours and prepare for some good, old-fashioned abuse at the “check-in”, where your tour leader will give you a taste of hospitality, USSR-style, when service with a snarl was the only way.

You’ll travel past Tallinn’s least attractive Soviet architectural sights—dismal, concrete apartment blocks and a former jail—and sample pickles and vodka shots as you clatter around on an ancient bus. This thoroughly entertaining experience ends with a singalong of Soviet-era songs.

Uncover the Secrets of the KGB

Exterior of Hotel Viru

Hotel Viru

One of the most intriguing things to do in Tallinn is to visit the KGB Museum, so be sure to book your slot for a deeper insight into the espionage that was rife in Soviet times. The tiny museum is actually a room in the Hotel Viru, once operated by Intourist and, when it was built in 1972, Tallinn’s only tower block.

KGB agents occupied a radio center on the secret 23rd floor from which they would spy on the foreign guests who stayed here. Needless to say, some 60 rooms and several of the tables in the restaurant were bugged. The Soviet spying gear that the KGB agents left behind when they fled in 1991 is the stuff of vintage James Bond.

Spot Seals in the Malusi Islands

Seal spotted in the Malusi Islands

Malusi Islands

If you feel you’ve done Tallinn, venture out of town into the beautiful Estonian countryside to a different world of bucolic scenery and sleepy villages seemingly forgotten by time. From the pretty port of Kaberneeme, you can take a boat to the Malusi islands, the habitat of several grey seal colonies.

Bizarrely, the seals are lured by classical music; Beethoven, Debussy, and Mozart will summon them to jump off their basking rocks into the water and swim around the boat. The tour is a great introduction to the mammals and seabirds of the Baltic.

Browse our wide range of cruises to Tallin to find the perfect voyage to this beguiling place.

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