Dive into Tallinn Old Town's Medieval Magic: Our Top 10 Experiences

Tallinn Old Town is one of Europe’s best-preserved medieval centres, yet it's far from a museum piece. Beneath its Gothic spires and within its cobblestone passageways, you’ll find a city alive with cafés, boutique shops, galleries and bars. It's both a UNESCO World Heritage Site and a living neighbourhood, where history and modern life rub shoulders. Here are our 10 top experiences that combine the classic must-sees with local secrets and practical tips for making the most of your visit.

At the heart of Tallinn Old Town, Town Hall Square (Raekoja plats) has been a gathering place for over 600 years. The Gothic Town Hall – northern Europe’s only surviving example – towers over the cobbles with its elegant spire, topped by the Old Thomas (Vana Toomas) weathervane, Tallinn’s guardian since 1530. According to legend, it was modelled on a peasant boy who won a crossbow contest but was denied the prize because of his rank. The city immortalised him as protector, and though today’s figure is a replica, he still surveys the rooftops.

The pastel-coloured merchant houses that line the square once served as medieval trading halls. Today, they’re home to courtyard restaurants, cafés and boutique shops. In summer, parasols fill the cobbles and the square hums with visitors. In December, it becomes the setting for one of Europe’s most atmospheric Christmas markets, with mulled wine, Estonian pastries and a towering spruce at its centre.

Tallinn’s medieval wall once stretched over 3 km, defended by more than 40 towers. Around half survive, making this one of the most complete city fortifications in Europe. Their red-tiled turrets and crenellated ramparts give Tallinn Old Town its fairy-tale outline.

The most evocative section is between the Nunna, Sauna and Kuldjala towers, in the northwest corner. Wooden staircases lead up to the covered walkway where watchmen once patrolled. From here, you can spy into hidden courtyards, gaze across church spires and picture what life might have been like when the wall bristled with guards. If you’re short on time, climb Kiek in de Kök (literally 'Peek in the Kitchen'), a 15th-century artillery tower that now houses a museum of the city’s defences.

Once thought to be the tallest building in the world, St Olaf’s Church (Oleviste kirik) is a Gothic marvel with a spire that pierces the skyline at 124 m. In medieval times, its soaring tower was used as a navigation marker for ships approaching Tallinn’s harbour.

Inside, the whitewashed nave is understated, but the real reason to visit is the climb: 232 narrow spiral steps to a 60-m-high viewing platform. The view is worth every step – a sweeping panorama across the Old Town’s rooftops, Toompea Hill and the Gulf of Finland beyond.

Tucked away behind Vene Street, the Masters’ Courtyard (Meistrite Hoov) is one of Tallinn’s loveliest hidden corners. Once the stronghold of medieval guilds, the cobbled courtyard still hums with creativity. Today, small workshops sell ceramics, jewellery and textiles. In summer, artists often sit outside at their benches, tools in hand, as visitors wander past.

Don’t miss the tiny chocolate shop, where locals stock up on handmade truffles and pralines. Sitting at one of the courtyard’s café tables with a hot chocolate feels like slipping into another century.

Perhaps the most photogenic street in Tallinn Old Town, St Catherine’s Passage is a narrow cobbled lane connecting Vene and Müürivahe streets. Its half-covered cloister wall and row of medieval tombstones lend a hushed, almost monastic atmosphere, yet the workshops that line it are full of life.

Here, you can watch artisans at work: glassblowers shaping molten forms, potters at their wheels and milliners stitching hats. It’s not just for browsing – many studios welcome questions and are happy to explain their craft. If you’re looking for authentic Estonian crafts rather than mass-produced trinkets, this is the place.

Tallinn may be best known for its Gothic spires, but the 19th-century Alexander Nevsky Cathedral is equally striking. Perched on Toompea Hill, its black onion domes and gilded crosses dominate the skyline. Built during Russian Imperial rule, it remains a working Orthodox church.

Step inside to find mosaics, gilded icons and richly coloured frescoes that contrast with the austere interiors of nearby Lutheran churches. At services, incense wafts through the nave and the choir fills the space with solemn song. The cathedral is free to enter. Remember to dress modestly and avoid taking photos during services.

Toompea Hill has always been Tallinn’s citadel of power. The pink Baroque façade of Toompea Castle today houses Estonia’s parliament, but its story stretches back to the 13th century, when the crusading Order of the Sword Brethren built their stronghold here. Walking around, you’ll notice the mix of medieval walls, bastions and later additions. The castle is not just a relic – it’s the beating heart of Estonia’s political life.

This quiet courtyard beneath Toompea Hill is steeped in legend. According to tradition, during a battle in 1219, the Dannebrog (Danish flag) miraculously fell from the sky, turning defeat into victory. Today, three cloaked monk statues loom in the shadows, giving the garden an eerie theatricality. Despite the drama, it’s also one of the best places to see the Town Wall and towers close up. Visit at dusk, when the statues are illuminated and the garden feels like a stage set.

Tallinn’s dining scene balances medieval atmosphere with contemporary tastes. In the Old Town you can sample traditional Estonian dishes such as elk stew or marinated herring, but also inventive modern menus.

• Rataskaevu 16: Beloved by locals for its warm service and seasonal cuisine.
• III Draakon: A medieval tavern inside the Town Hall serving rustic snacks like elk soup — inexpensive and fun.
• Farm: Combines Estonian ingredients with modern presentation in a stylish setting.

For a quieter meal away from the crowds, try one of the restaurants in the courtyards off Vene or Müürivahe streets.

If you want to immerse yourself fully, staying in the Old Town is ideal. Cobblestones and spires will be on your doorstep, and you can enjoy the early mornings and late evenings when the day-trippers have left.

• Swissôtel Tallinn: Modern luxury with sweeping city views and easy access to both Old Town and the creative Kalamaja district.
• Mövenpick Hotel Tallinn: Surrounded by shops, bars and restaurants, it blends contemporary comfort with a nod to Tallinn’s heritage.
• Novotel Tallinn: A four-star property in a prime central location, perfect for travellers seeking modern convenience steps from history.

Tallinn Old Town is not just a historic centre frozen in time. Its cobbled streets and watchtowers coexist with vibrant cafés, lively market halls and creative districts. Whether you linger in a medieval courtyard, walk the city walks or climb a Gothic spire, the city rewards both first-time visitors and seasoned travellers. And by combining your exploration of Tallinn’s medieval heart with a stay in one of its well-located hotels, the Old Town will feel like your own neighbourhood, with every turret and tapestry just a short walk away.