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Tallinn Old Town could be lifted straight from the pages of a pop-up fairytale book. Spread across two levels, the Lower Old Town and Upper Toompea Hill, the enchanting tangle of tapered cobbled lanes, steepled cathedrals, and leafy courtyards constitutes one of Europe’s best-preserved medieval cities.

Locally known as Vanalinn, the entire historic core is classified as a UNESCO World Heritage Site. From its 13th-century Hanseatic League trading roots and defensive towers to more recent subsurface tunnels and Soviet-era additions, storied corners abound. Not that it’s all tales of yore; today, the Old Town is thriving with local produce restaurants and green spaces beloved by residents.

Whether you’d prefer to experience the Estonian capital’s oldest quarter in medieval dining rooms, underground military tunnels, or turrets-turned-museums, here’s everything you need to know to plan the perfect Old Town Tallinn visit.


Toompea Castle

Historic site of Toompea Castle

Toompea Castle

While the lower section of Tallinn Old Town was home to merchants and common folk, Toompea Hill was reserved for the affluent. From here, peering down on those below, both literally and figuratively, the nobility of Tallinn had the best views of the Old Town.

Unsurprisingly, it was here that all of the city’s various rulers decided to build their castles and stately residences. The layers created by these monarchs and occupiers are stacked high, with the current Toompea Castle built atop the ruins of an 11th-century fortress.

Toompea Castle in Tallinn Old Town

Toompea Castle

Thankfully, the most recent 18th-century Baroque complex, now home to the Estonian parliament, isn’t reserved solely for those in power and can be visited on a guided tour. There’s even a viewing gallery to see the nation’s lawmakers at work.

More interesting still is to learn about the site’s Livonian, Danish, German, Swedish, and German occupations with a guide, who will share tales and tidbits on a stroll through rococo state halls and gothic quarters.

Fat Margaret

Historic tower of Fat Margaret

Fat Margaret

The towers of Tallinn Old Town have more than served their purpose over the years. Some, such as the curiously named Fat Margaret—perhaps named for a plump former staff member or suitably fearsome cannon, depending on who you ask—have now been repurposed as museums.

Once a former gunpowder store and prison, Fat Margaret is now an outpost of the Estonian Maritime Museum. Its four floors display a varied collection of seafaring stories and memorabilia.

With so much of Tallinn’s importance linked to the sea and trade, the collection is as fascinating as the structure itself, with artifacts and plenty of ship recreations. Yet the star is the weathered and beaten hull of a 700-year-old vessel, the Koge, which was only discovered on a nearby building site in 2015.

Alexander Nevsky Cathedral

Unique architecture of Alexander Nevsky Cathedral

Alexander Nevsky Cathedral

St. Alexander Nevsky Cathedral is one of Vanalinn’s more recent editions, only completed at the turn of the 20th century. Bringing a new dynamic to Toompea Hill, the Russian Orthodox church was one of the last buildings constructed when Tallinn was part of the Russian Empire.

It’s quite the sight, with its five onion-shaped domes crowning the ornately decorated exterior, adorned with golden mosaics depicting religious and Russian characters. Step inside and the spectacle continues, with gilded altars and more mosaics highlighting the empire’s wealth.

On a well-timed visit, you’ll be serenaded by the ringing of the cathedral’s 11 bells, which chime melodically as a call before services.

Kiek in de Kök Museum

Fairytale like tower of Kiek in de Kök Museum

Kiek in de Kök Museum

Tallinn’s historic center is gorgeous from all angles, but for a closer inspection of the medieval city, plan an underground exploration at the Kiek in de Kök museum.

Bundling together some of the most interesting parts of the newer defenses, including a set of subsurface passages from the 17th century, the museum provides an understanding of the region’s volatile past.

Join a guided tour of the bastions to gain an insight into military life underground. There’s also an excellent museum in the tower dedicated to military events from the 13th to the 18th century, with all the armor, cannons, and artillery artifacts you’d expect.

Pay particular attention to the tower’s walls, still embedded with 16th-century cannonballs fired under the orders of Ivan the Terrible.

View of Danish King’s Garden

Danish King’s Garden

Post-visit, pause in the Danish King’s Garden, overlooked by Neitsitorn, or the Maiden’s Tower. Continuing the theme of all those who have been and gone in Reval, as Tallinn was once called, this peaceful pocket, often with medieval-outfitted performers, is named in remembrance of when Estonia was part of the Kingdom of Denmark.

Viru Gate

Viru Gate in Tallinn Old Town

Viru Gate

Tallinn’s Old Town walls are one of the city’s greatest architectural achievements, and the still-standing sections serve as a reminder of just how mighty and prosperous Vanalinn once was.

Yet perhaps even more striking than the walls themselves are the towers and imposing gates. None are more impressive than Viru Gate, an imposing, twin-towered entrance once crossed by horse-drawn carts transporting goods to the central market.

Nowadays, it still provides an excellent introduction to the Old Town. Stroll along Viru Street, with its superb choice of stores—Andry’s Antiques has some wonderfully quirky collectibles—to follow in the footsteps of medieval merchants towards Tallinn’s Town Hall Square.

Things to Do in Tallinn Old Town

Walk the Old Town Walls

Historic Old Town Walls of Tallinn

Old Town Walls

Viru Gate might be the city’s grandest entrance, but for a more intimate experience of Tallinn’s Old Town Walls, or Linnamüür, you can’t beat walking on top of them.

Once, the whole city was encircled by these sometimes 45-foot-high walls dotted with watch towers. More than half of the walls remain intact today, but only a small section can be accessed by the public.

Bridging the Nunna, Sauna and Kuldjala towers, the walkable section is one of the most impressive, thanks to the restoration of the 13th-century stonework and pointed-roof towers. As with any elevated point of the Old Town, gorgeous views are a dime a dozen. Just be prepared for the incredibly narrow staircase.

Explore Medieval Streets & Courtyards

Medieval streets of Tallinn Old Town

St. Catherine’s Passage

One of Vanalinn’s greatest joys is detouring down alleyways and stumbling upon practically unchanged medieval corners. Half-timbered homes embellished with calligraphy signs, tapered streets leading to picturesque courtyards, and former merchants’ houses all contribute to this storied center.

Slip down St. Catherine’s Passage, one of Tallinn’s most emblematic streets, to spot the walls of a medieval monastery and typical craft workshops still in use today.

Then, venture to the Masters’ Courtyard for a hot chocolate at Pierre Chocolaterie, the cafe’s colorful fabric-clad tables spread across the ancient stone floor. But be sure to leave some time to amble aimlessly, always looking up to spot emblems among the gables.

Climb the Town Hall’s Tower

Town Hall Square in Tallinn Old Town

Town Hall Square

Raekoja Plats, Tallinn’s Town Hall Square, remains very much the city’s meeting place, having served as a market for centuries. Nowadays, the square is flanked by restaurant terraces ideal for a scenic lunch, especially in the warmer months when a “garden park” of benches, bucket chairs, and greenery takes over, often soundtracked by buskers.

The square’s most outstanding feature is the Gothic Town Hall, topped by a weathervane depicting Old Thomas, a legendary countryside character. While you shouldn’t skip the medieval museum inside, the main attraction is the 210-foot-high tower. Ascend the staircase to the balcony around halfway up to fully appreciate Raekoja Plats’ grandeur.

Capture the Perfect Panorama

Scenic view from the Patkuli Viewing Platform

View from the Patkuli Viewing Platform

For the most camera-friendly cityscapes of Old Town Tallinn, ascend to the Patkuli Viewing Platform in Toompea Hill. Peering over the balcony’s edge, the Old Town’s many soaring spires and conical towers unfurl towards the Baltic Sea. From here, you can fully appreciate how vast the city’s defensive walls once were.

One of the best things to do in Tallinn is to visit the Kohtuotsa Viewing Platform, offering a slightly different vantage point. With much the same views towards the Gulf of Finland, this balcony also affords views of St. Nicholas’ Church.

Tour Tallinn’s Churches & Climb Spires

Street view of St. Nicholas

St. Nicholas

Even given the generous proportions of Tallinn’s Old Town, the number of churches is impressive. There are over a dozen, spanning various centuries and architectural styles.

While you’ll be hard-pressed to visit them all, you shouldn’t miss those with Tallinn’s signature steeples providing show-stealing panoramic views.

Although heavily restored, St. Nicholas is one of Tallinn’s best examples of Gothic architecture. Inside, the Niguliste Museum displays religious art from the Middle Ages, including the surviving 23-foot section of Bernt Notke’s haunting Danse Macabre canvas, originally four times as long. St. Nicholas’s newly opened glass lift allows easy access to the steeple’s viewing platform.

Beautiful landscape of St. Olav’s Church in Tallinn Old Town

St. Olav’s Church

For further panoramic moments, requiring a little more effort, 16th-century St. Olav’s Church lauds the loftiest steeple in the Old Town. You’ll need to climb 232 narrow stone stairs to reach the viewing platform, but the breezy views are a magnificent reward.

Visit the Museums

Exterior of the Estonian History Museum

Estonian History Museum

Many of Tallinn’s best museums are concentrated in the Old Town, occupying medieval merchants’ houses and historically significant buildings.

For a deeper dive into the city’s history through the ages, the Tallinn City Life Museum tells the stories of its residents through quirky temporary exhibitions and a permanent collection covering everything from maritime trade to medieval torture instruments. The 15th-century Great Guild Hall, now the Estonian History Museum, provides a more country-wide account.

If you’d prefer a niche lesson on Estonian life, Tallinn doesn’t disappoint. The diminutive Banned Book Museum offers some fascinating local insights, while the dingy, subsurface KGB Prison Cells share stories of those who suffered at the hands of the Soviet regime.

Restaurants in Tallin Old Town


Seconds from one of Toompea Hill’s best vantage points, Fersen is an inviting mix of exposed, flaking brickwork and original fireplaces. Though on a sunny day, the terrace provides some stiff competition.

Take your pick from traditional dishes befitting of the medieval ornamentation, such as elk dumplings paired with a horseradish liquor or bread-topped, well-seasoned fish soups. If you’ve no space left for dessert, wash your meal down with a glass of warm, spiced Glögg.

Peet Ruut

In this cozy restaurant of unvarnished wooden tables and splintered ceiling beams, all bathed in warm tones from mismatched lamps, you can expect one of Tallinn’s best dining experiences.

The menu is succinct but delicious, with a focus on eastern European recipes blended with modern flair. Locally sourced, organic ingredients are standard and the dishes’ presentation is as pretty as the restaurant itself.


Exterior of Troika restaurant

Troika Photo by Pete on Flickr, licensed under PDM 1.0

With a terrace on Town Hall Square, Restaurant Troika is an excellent place to watch the world pass by. However, the real magic is inside. Cross the threshold to step back in time; the vaulted ceilings and tavern-style bar laden with trinkets create quite the setting.

Add vodka poured from high at the table, traditional Estonian outfits, and occasional live music, and you’re all set for an entertaining lunch. Venison-stuffed dumplings, slow-cooked lamb shanks, and hearty soups in earthenware bowls ensure the menu matches the medieval theme.


Italian food might not be your first craving in Estonia, but this gorgeous, weathered restaurant with arched doors and wooden beams is one of Tallinn’s most aged dining rooms.

Set on historic St. Catherine’s Passage, Controvento is the perfect spot to enjoy a plate of Italian pasta in a typically medieval setting. Still, you’ll find some Estonian ingredients on the menu, with foraged mushrooms, hare, and deer all featured.

Café Maiasmokk

Street view of Café Maiasmokk

Café Maiasmokk Photo by Felipe Ernesto on Flickr, licensed under CC BY 2.0

The oldest café in Tallinn Old Town, and indeed Estonia, Café Maiasmokk is the perfect place to pause for coffee and cake between sightseeing. With dark wooden cabinets, embellished faded-gold wallpaper, and ornately decorated ceiling panels, it’s a true time capsule.

But with café culture flourishing on every corner of Estonia’s capital, what makes Maiasmokk stand out? Marzipan.

Doubling as a museum dedicated to almond candy dough, you can watch the popular and once believed to be medicinal fancies being painted. For a special souvenir, purchase one of the cafe’s self-decoration marzipan boxes to take home.

Travel Tips

Getting to Tallinn Old Town

Town Hall Square in Tallinn Old Town

Town Hall Square

Being the heart of this European capital city, it’s impossible to miss Tallinn Old Town. The city has a good bus and tram network linking other districts. Most of the Old Town is pedestrianized, however, making it a joy to explore on foot.

Best Time to Visit

Colorful buildings in Town Hall Square in Tallinn Old Town

Town Hall Square

With Baltic winters and long, merry summer days, the best time to visit Estonia is May until September. During these months, the weather is more reliable, and Tallinn Old Town is at its most spirited thanks to the al-fresco dining terraces, which bring more of an outdoor atmosphere.

What to Pack

Couple exploring the Old Town of Tallinn

Tallinn Old Town

Even in summer, it’s best to visit Tallinn Old Town prepared. You’ll want to pack layers, including a coat and perhaps even an umbrella in case of unexpected showers.

Most importantly, bring a pair of comfy walking shoes. Not only are the stairs up to Toompea Hill quite the climb, but you’ll want to feel comfortable as you explore Tallinn’s many layers, whether it’s the cobbled alleys or underground tunnels.

Currency & Tipping

Estonia, like much of Europe, uses the euro (EUR). Being one of the world’s most forward-thinking nations, cryptocurrency is also becoming an accepted payment method in some businesses and paying by card is rarely an issue.

A tip isn’t expected as standard in Tallinn. However, leaving five to 10 percent is appreciated if you’ve had great service.

What to Buy

Potions at an old pharmacy called Raeapteek


Tallinn Old Town is a delightful place to shop, especially because Estonians passionately support local artisans. For bold, hand-crafted jewelry, pop into A-Galerii, a century-old store that sells statement pieces crafted by local designers.

Masters’ Courtyard, with its small clutch of handicraft stores, is an excellent place to buy Estonian embroidered linen. Be sure to peek inside Raeapteek, one of the world’s oldest pharmacies, where the wooden display cases are stacked with medieval potions, apparently heartache-curing marzipan, and “medicinal” spiced wines.

Couple sightseeing from Town Hall Square

Town Hall Square

Ready to walk Old Town Tallinn’s medieval walls and get lost among a labyrinth of storied cobblestones? Browse Celebrity’s Tallinn cruises to plan your thrilling vacation around the Baltic Sea.

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