Walking through Tallinn, you realize that it’s a city of ancient legends and beliefs, each street breathing with centuries-old tales. However, Tallinn has managed to embrace not only medieval traditions but also a modern perspective on the world. Young creative individuals and seniors alike stroll along the sidewalks, while ultramodern boutiques, stylish bars, and restaurants inhabit the historic buildings. Let’s take a stroll today through the most wonderful locations in the old town of Tallinn.
An interesting fact is that the city was known by different names in the past – Kolovan, then later Revel, and only in 1917 did the Soviet government rename it Tallinn, meaning “Danish city.”
Tallinn welcomes with its friendliness and gives off the impression of a city from childhood fairy tales, now accessible to all adults. The city surprises with its unique atmosphere: serving elk pastries, offering liqueur, and dancing medieval dances.
From the Soviet past, almost nothing remains, except occasional Russian speech and signs in Russian on shops; otherwise, it’s a European city with its own quirks.
I love everything here: the architecture, entertainment, people, and local cuisine. Neat, well-kept, and very European. You can feel the old good Europe in everything, but trying to find the Soviet Union is futile: neither in the streets, nor in the squares, nor in the houses – it’s simply not there.
Tallinn has a fashion for medievalism, and it’s evident from the first moment you walk around the city. Ancient churches, quaint streets, girls dressed in medieval garb and young men selling medieval paraphernalia. There are musicians and jesters walking past beer “pubs”, but this is not a tribute to antiquity, but rather a great idea to make money from gawkers like me. In any case, I like it very much… uhhhh!
Must-see locations in the Old Town of Tallinn.
The old town of Tallinn is quite small, and most streets have retained their quirky architecture. It’s an island of medieval life in the heart of the city.
The old town is divided into two parts: Upper Town, home to Toompea Castle, Alexander Nevsky Cathedral, and St. Mary’s Cathedral, and Lower Town – more vibrant with entertainment, housing the medieval Church of St. Olaf.
St. Olaf’s Tower (124 m) was once considered the tallest tower in the world, and today it’s the tallest building in the city. Just imagine, it was once the biggest in the world, in the WORLD! Nowadays, there are all those Burj Khalifas, but once this tower was considered an immense skyscraper. And it will remain so for a long time, as building higher than this tower is prohibited in the city.
On the main square stand a sweet pair of houses – numbers 15 and 16. They are almost the main symbols of Tallinn. Postcards, magnets, mugs, T-shirts, and other souvenirs are sold with these houses.
On the Town Hall Square there is a stone resembling a sewer manhole, from which you can see all 5 main spires of the city. From here you can also see the Town Hall and its protector, Old Thomas. Thomas was erected in 1530, but was destroyed in a bombing raid during WWII. The locals had to reinstall the chap, who still keeps the town safe to this day. More interesting locations in the Old Town of Tallin?
While walking through Tallinn, you may come across a medieval pharmacy, where on the shelves lie ancient remedies in the form of bats, mummy juice, snake elixirs, unicorn horn powder, worms, and toads. In reality, it’s an ordinary pharmacy selling common medicines. But there’s a separate shelf with all sorts of nastiness that attracts tourists like a magnet. The pharmacy is popular because it has never closed for 600 years. Address: Raekoja plats 11.
On one of the streets, you stumble upon another interesting building – a very unusual grocery store. For example, a jar of pickled cucumbers here is called “Good Morning,” and next to it lies wild boar sausage and canned beaver meat. While it may be created for the entertainment of visitors, it’s what makes Tallinn memorable as a truly original city.
Wandering through the center, you spend a long time examining every detail of the houses. Each building here is unique and deserves individual attention. Only here do you find doors of unusual shapes. Have you noticed that many roofs have ropes with hooks hanging from them? Ever wondered why? It’s quite simple: these narrow doors cannot accommodate large furniture or bulky items. Usually, behind the door is a narrow passage with a small staircase, so people hoist many things using this hook, attaching the load to it. By the way, Tallinn is not the only city that employs such a trick. This phenomenon has been observed in Warsaw, Riga, and Paris.
You must visit the Kohtu viewing platform – here you’ll undoubtedly get the best view of the city – red-tiled roofs and the blue Baltic Sea. Come here during the day, and even better, go in the evening when everyone has dispersed. The little Carlson in me finds happiness here.
In the fairytale Tallinn, surrounded by a stone wall, there’s a sense of age-old solidity and prosperity. The restored and painted medieval houses are welcoming and friendly. People are sociable and smiley. The cobbled streets are wide and tidy.
But turn down an inconspicuous alley or back alley and the distance between the houses narrows, sometimes to such an extent that even a car cannot pass. Here another side of Tallinn is revealed, the houses are not so beautiful anymore. They are even frightening with their medieval brutality and abandonment. Especially at night. Walking through these small alleys in the dark, where only small, barely glowing lanterns are lit, and even then not everywhere, you feel like a medieval passer-by. And drunken sailors with a half-drunk bottle of rum are just around the corner.
Here, you understand that it’s the embodiment of the childhood dream of Potterman: there are so many nooks, secret streets, and hidden passages. You won’t find anything like this in Italy, and believe me, Italians are masters of mazes!
Walking through Tallinn, you inevitably begin to compare the city with other European cities. Prague, Copenhagen, how many similar cities are there in Europe? In the Middle Ages, different countries had the same architectural styles; they bridged streets, built houses, bridges alike. The infrastructure for tourists is equally developed and convenient today. But during the Soviet era, Tallinn replaced Stockholm and Munich for film directors. The city has European charm, but there’s slightly less of it here than in other European cities. Tallinn is more provincial than, for example, Helsinki, and there are clearly more Russian speakers here.
On weekends, Tallinn is flooded with Europeans. Its streets and drinking establishments are “occupied” by Finns who come to Estonia for entertainment. It only takes them two hours by ferry. And alcohol is much cheaper here than in Helsinki. Estonians are considered the most drinking nation, with 50 bottles of vodka per person per year, including sick and pregnant people, by the way. But Estonia is completely covered by a Wi-Fi network, and Skype was also invented here.
If you have free time, take a ferry trip to the neighboring country, Finland, and visit Helsinki. You can also add a trip to Suomenlinna Island to your journey, which is located near the Finnish capital. You can reach it by a small boat in just a few minutes.
Where to eat in Tallinn?
After exploring all the main locations in the old town of Tallinn, your feet will naturally take you to the Town Hall Tavern “III Draakon.” When you enter here, you feel like you’ve been transported back 300 years. Everything is decorated in medieval style, and there’s no artificial light here. The café is fully lit by candles, and there are pickled cucumbers floating in a barrel that you can fish out and eat until you burst. Just like 500 years ago, they treat you with the most delicious meat pies made of venison here. It’s worth washing them down with A. Le Coq, a local Tallinn beer. Prices in the city are quite high, and this restaurant is one of the cheapest. There are no spoons here as in ancient times, and you’ll drink soup from a cup.
Another equally popular restaurant is “Olde Hansa” on Vana Turg Street. The restaurant in medieval style complements the impressions gained during the day from walks around the Old Town. Everything here is medieval: the serving staff – waiters in costumes appropriate to the era; the atmosphere – roughly hewn wooden tables and benches, wooden walls, subdued lighting; the serving – clay bowls, clay mugs, and clay shot glasses. In drinks – beer with caraway or herbs, vodka infused according to a special recipe. In food – wild boar, game, turnips, pickles, bread, and – no potatoes. In music – musicians in medieval attire walk through the halls and sing medieval music.
I hope you enjoyed these locations in the old town of Tallinn as much as I did and have a good time here!
How to get to Tallinn.
In this guide, we’ll explore various transportation options to help you reach Tallinn hassle-free.
By Air: The most convenient way to reach Tallinn from international destinations is by flying into Tallinn Airport (TLL). It’s the largest airport in Estonia and serves numerous airlines connecting major European cities and beyond. Once you land, you can easily reach the city center via taxi, bus, or even by using ride-sharing apps like Bolt.
Check Aviasales to find the cheapest flights to Estonia if you’re traveling from another country.
By Sea: If you’re coming from Finland, hopping on a ferry from Helsinki to Tallinn is a popular choice. The journey takes around 2 to 3 hours, offering stunning views of the Baltic Sea along the way. Several ferry companies operate on this route, providing multiple daily departures. Once you arrive at the Tallinn port, you’re just a short distance away from the city center.
Tallinn is a common stop for Baltic cruises, allowing travelers to explore the city’s highlights during a day trip. Cruise ships dock at the Port of Tallinn, which is conveniently located near the old town. While this option is great for a brief visit, if you want to delve deeper into Tallinn’s culture and history, consider extending your stay.
By Bus: Estonia boasts an efficient bus network, connecting Tallinn with neighboring cities and countries. International bus services operate from major European cities such as Riga, Vilnius, St. Petersburg, and even Warsaw. The bus station in Tallinn is located close to the city center, making it convenient for travelers to explore upon arrival.
The most authentic hotels in Tallinn.
Tallinn, the capital city of Estonia, is a place where medieval charm blends seamlessly with modern sophistication. Its cobblestone streets, centuries-old buildings, and vibrant culture attract travelers from all over the world. While exploring this enchanting city, locations in the old town of Tallinn, immersing oneself in its authenticity is key to truly experiencing its essence. And what better way to do so than by staying in hotels that embody the spirit of the city?
Hotel Telegraaf: Nestled in the heart of Tallinn’s Old Town, Hotel Telegraaf seamlessly combines historical elegance with modern luxury. Housed in a former telegraph exchange building dating back to 1878, this five-star hotel exudes charm at every turn. From its meticulously restored façade to its elegantly appointed rooms, Hotel Telegraaf offers a glimpse into Tallinn’s rich past while providing guests with all the comforts of contemporary hospitality. The hotel’s spa, housed in the building’s former vaulted cellars, is a tranquil oasis where guests can unwind after a day of exploring the city.
Schlössle Hotel: Tucked away on a quiet cobblestone street, Schlössle Hotel is a hidden gem in Tallinn’s Old Town. This boutique hotel occupies a beautifully preserved 13th-century merchant’s house, where every corner is steeped in history. Each of the hotel’s rooms and suites is uniquely decorated with antique furnishings and modern amenities, offering guests a truly immersive experience. The hotel’s award-winning restaurant, Stenhus, serves up exquisite Estonian cuisine in a cozy, candlelit setting, making it the perfect spot for a romantic dinner or special occasion.
The Three Sisters Hotel: Housed in a trio of meticulously restored medieval merchant houses, The Three Sisters Hotel is a true architectural marvel. Located just steps away from Tallinn’s iconic Town Hall Square, this boutique hotel offers a seamless blend of historic charm and contemporary comfort. Each of its 23 rooms and suites is individually designed to reflect the building’s rich heritage, with exposed wooden beams, original fireplaces, and luxurious furnishings. The hotel’s cozy courtyard garden provides a peaceful retreat from the hustle and bustle of the city, while its onsite restaurant, Bordoo, serves up innovative Estonian cuisine with a modern twist.
You’ll want to come back to Tallinn again and again. It’s truly one of those few cities that you want to see twice, three times, or even more times. Tallinn is like a time machine that takes you back through the centuries.
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