Estonia's capital Tallinn has a lot to offer, but its charming Medieval Old Town is by far its main attraction. Centuries-old buildings topped with red roofs, half-hidden courtyards, cobblestoned streets surrounded by an almost intact wall dotted with guard towers—it is a UNESCO World Heritage site and Tallinn's pride.

The Old Town is compact and can be easily explored on foot. But what is the best route to take in order to see everything? The following walking tour includes most of the Old Town highlights, as well as a coffee break and hand picked lunch recommendations. If you start the tour around 8 or 9 o'clock in the morning, you will have time for a leisurely lunch and then spend the afternoon shopping for souvenirs or visiting galleries and museums.

Google maps will help you follow the route and all sights and restaurants mentioned in this post are very easy to find.


Start your walking tour on the Town Hall Square (Raekoja plats), the undisputed hub of the Old Town for the last eight centuries. Surrounded by elaborate merchant houses and outdoor cafés, it is a natural magnet for tourists.

The impressive 14th-century Gothic town hall dominates the square, but do not miss Raeapteek, the oldest operating pharmacy in Europe (since 1422) on the corner of Apteegi Street. During the medieval times you could buy anything from snakeskin potion and mummy juice to marzipan over here. It was so famous in its day that even the Russian tsar used to order medicines from here. It still operates as a pharmacy today and has a small museum with an interesting display of 17th- to 20th-century medicinal bric-a-brac.

Tallinn old town walking tour


Around the corner from the Town Hall is the spectacular St. Nicholas Church (Niguliste kirik, you can see it on the picture above). It is a former church that now houses a museum and a concert hall. Its most famous exhibit is the impressive 7.5-meter  "Dance Macabre" painted by Bernt Notke at the end of the 15th century.

The museum's shop is a good place to buy quality souvenirs and mementos form Tallinn. Check whether they have any concerts during your stay. It is a gorgeous venue and you can hear world-class music in Estonia.

Tallinn old town waling tour


When you leave the museum, turn left and take the steps up Lühike jag (Short Leg) towards Toompea Hill. There are a couple of galleries and souvenir shops on the way up.

Just before the large wooden door, step into the Danish King's Garden. Take a selfie with a faceless monk and have a coffee at the Virgin Tower (Neitsitorn). The café has tables along the town wall offering spectacular views of the garden and the Old Town.

The neighboring Kiek in de Kök Cannon Tower displays and exhibit about the birth of the town, the history of its fortifications and main military campaigns from the 13th to the 18th century.

Here is also the entrance to the Bastion Passages—the underground tunnels from late 17th and early 18th centuries that were built to conceal the redeployment of troops from one site to another during the Great Northern War. For Estonia, the war resulted in the change of power from the Kingdom of Sweden to the Russian Empire.

Continue your tour going up to Toompea Hill.


Tallinn's Old Town consists of two parts: the upper town and the lower town. When the lower town is where the merchant houses were located, then the upper town, Toompea, is where the nobility lived. Lower town is also where the hustle and bustle, the shops and the restaurants are while Toompea is much more quiet.

Toompea's top attractions are Toompea Castle, Dome Church, Nevski Cathedral, and the viewing platforms. When you reach Toompea, you will see the pink parliament building with the Tall Hermann Tower in the background, while the most noticeable structure on this square is the Alexander Nevski Cathedral.


Walking tour of Old Town Tallinn


Toompea Castle, towering over the city, was built in the early 13th century and has always been the seat of power in Estonia. If you walk down Toompea Street to the corner of Falgi Street, you can see the oldest part of the castle surrounded by the town wall. The pink, Baroque palace that forms the front of the castle complex dates to the time when Estonia was a province annexed by the Russian Empire. It is now home to the Estonian Parliament.

To the left of the castle, is the Governor's Garden where the 46-meter Tall Hermann tower (Pikk Hermann) comes into view. The tower is an important national symbol: each day at sunrise the Estonian flag is raised above the tower to the tune of the national anthem.

The onion-domed, opulent Alexander Nevski Cathedral sits in the middle of the square. It was built in 1900, during the time when Estonia was a province of the Russian Empire. The cathedral was intended as a symbol of its political dominance in this unruly part of the empire. Tourists love it, Estonians not so much.


Just steps away from the Castle Square is the beautiful Dome Church or Cathedral of St. Mary the Virgin with its Baroque spire. The original church was built in 1229 but it has undergone several renovations and the current, Gothic structure originates from the 15th century. Old tombstones and elaborate coat-of-arms of noble families can be found here, as well as the wood-carved pulpit and the altar. There may be an organ recital that you can enjoy if you happen to be there on a Saturday morning.


When you leave the cathedral, turn to your left and take Kohtu Street to the Kohtuotsa viewing platform. Here, you can enjoy views over the red roofs of the old town and the new town in the background. Then bear to your right to go to the Patkuli viewing platform for the most magnificent views of the town wall and the sea. To the left of the Patkuli platform is where the Estonian Prime Minister's Office is located. The beautiful building is one of the best examples of classicist architecture in Tallinn.

Walking tour of Tallinn Old Town

Now take the steps down—that is 157 steps zigzagging down—back to the lower town. Cross Nunne Street and bear to the left to walk through the Towers' Square (Tornide väljak), on the outer side of the town wall. Here, you will have a beautiful view of some of the defensive towers of the city.

Walking tour of Tallinn Old Town
Walking tour of Tallinn Old Town

Find the small passage through the town wall (before Suurtüki Street) that leads to Aida Street. Aida is a short street that looks the most like it was back in the Middle Ages. Pass the City Theatre’s summer stage on the left and turn to the left onto Lai Street. Don't miss the fine example of a merchant's house on the left at Lai 23 that is home to the City Theatre.


It is hard to miss the 124-meter spire of the 16th century Gothic St. Olaf's Church. Climb up the 258 steps to the top of the stone portion of the tower for magnificent and dizzying views of the Old Town, Toompea, and the port area. Unfortunately, the church is closed for renovations at the time of writing this guide.


Take Oleviste Street to Pikk Street. On the corner of Oleviste and Pikk, you will find three charming medieval merchant houses called the Three Sisters, home to the Three Sisters Hotel. Also on this end of Pikk Street are the Great Coastal Gate (Suur Rannavärav) and the Fat Margaret Cannon Tower (Paks Margareeta). The spectacular 25-meter-diameter Fat Margaret, with walls that are five meters thick, was built in 1501 and provided protection to the city from the seaward side of the town. The tower is home to the Maritime Museum, closed for renovations until November 2019.

Now turn back to Pikk Street and walk toward Town Hall Square. A block from the Three Sisters is the former KGB HQ in Tallinn, a majestic building with a horrible history that has been turned into luxury residences. In the cellar, though, you can visit the former prison cells at Pagari 1.


Pikk Street (Long Street ), is not only the longest street in the Old Town, but also the oldest one having existed for at least a 1,000 years. During the Middle Ages, it was the primary street that led from Toompea to the sea. The 1.2-kilometer street is lined with charming cafés, shops, and art galleries and has some fine architecture from medieval to Art Nouveau.

Look for some fine examples of Gothic architecture at Pikk 24 (St. Olaf's Guild Hall) and Pikk 17 (Great Guild Hall), as well as one of the few Renaissance buildings in town, the House of the Blackheads (1597) located at Pikk 26 with its ornately carved details and intricately decorated, red, green and gold door. The pearl of Baroque architecture  from 1670s can be found at Pikk 28 (von Rosen Palace), while Pikk 18 and 23/25 showcases some remarkable Art Nouveau architecture from the early 20th century.

Stop when you reach the small square lined with Maisamokk Café, the Great Guild Hall and the Church of the Holy Spirit.


The Great Guild Hall is one of the most distinguished buildings in the Old Town. The 15th-century building with its large porch and lion’s head door knockers houses the Estonian History Museum, covering Estonia's history from prehistoric times to the end of the 20th century.

Membership of this Hanseatic-era guild was limited to married German merchants who also controlled the Town Council. Check out the museum's exhibit, 'Power of the Elite' to learn about the history of the building.

Across the street is the famous Maiasmokk (Sweet Tooth) coffee shop, known for its sweets and marzipan.


The radiantly white 14th-century Holy Spirit Church across the Guild Hall is a spectacular structure inside and out, from its wood interior to the elaborate painted façade clock. The clock is Tallinn's oldest public timepiece dating to the late 17th century. Step inside to see the carved wood interior that includes such treasures as a unique 15th century altar by the famous Lübeck artist Bernt Notke (same artist who painted the Dance Macabre), and one of the oldest pulpits in Estonia, dating to 1597.

Walking tour of Tallinn Old Town


There is still more to see but if  you need a break, here are some hand picked and tested restaurant recommendations, all nearby.

In front of the Great Guild Hall is the Viennese-style Maiasmokk Café, Tallinn's oldest from 1864. Head to the lower floor for some superb pastries or to the upper floor for lunch.

Or, take Saiakangi Street to the Town Hall Square and sample some contemporary Estonian cuisine at Kaerajaan. The restaurants are touristy and mediocre at most on the main square, but Kaerajaan is an exeption. Also, around the corner from the square, across from St. Nicholas Church is Restoran Pegasus which prides itself for seasonal dishes and the freshest ingredients.

If you are curious about what people ate in the Middle Ages, head to Olde Hansa around the corner from the Town Hall. Here, dishes are cooked using 15th century recipes for a true medieval experience.

Some fine-dining restaurants like Cru, Dominic, and Ribe are located in the Town Hall-Vene Street-Viru Street triangle—all excellent choices for lunch. The charming passage off Vene Street, Katariina käik, is home to a great Italian restaurant, Controvento.

Telegraaf Hotel on Vene Street is home to one of Tallinn's best restaurants, Tchaikovsky,  and their summer terrace is a charming place to enjoy some of their delightful menu items.

St. Catherine's Passage

How about some after-lunch retail therapy? The small passage connecting Vene and Müürivahe Streets is called the St. Catherine's Passage, one of the most picturesque medieval streets in the Old Town. It is also home to the St. Catherine's Guild, a collection of artisan workshops where you can see the artists create and sell ceramics, hats, glassware, hand-painted silk and leather goods.

The street leads to Müürivahe Street where you can climb up Hellemann Tower, a 14th-century tower with access to a 200-meter stretch of Town Wall with fantastic views.

Walking tour of Tallinn Old Town

You can by all your woolen mittens, socks and sweaters in the shadows of the town wall on Müürivahe Street. Souvenir stores are also here but head to Viru Street for the best one. Turn left toward Viru Gates and check out the souvenir and handicraft store Hää Eesti Asi at Viru 23.

Walk by the flower stalls and head to Viru Keskus Shopping Center for some more retail therapy; take Viru Street back to the Old Town for some more exploring, or head to Liberty Square (Vabaduse plats) to see the War of Independence Victory Column and visit the Tallinn Art Hall.

The Kiek in de Kök Museum (see above) is just up the steps behind the Victory Column and if you walk further, you'll get to the Museum of Occupations.

Walking Tour of Tallinn Old Town