Tallinn: 36 Hours in Estonia’s Medieval Marvel

As part of our summer road trip in the Baltics, we visited the capital cities of Estonia, Latvia, and Lithuania, finding each city to have its own distinctive charm. The far northern part of our journey brought us to Estonia’s capital, Tallinn, a city with a medieval core on the coast of the Baltic Sea. Tallinn has long been a strategic port—playing a crucial role in east-west trade as part of the Hanseatic League in the 13th-16th centuries, serving as the chief port of the Russian Empire in the 19th century, and as the top grain handling port by the USSR during post-WWII occupation. 

Emerging from Soviet occupation in the 1990s, Estonia quickly moved to catch up with—and eventually surpass—the rest of the world in digital infrastructure. Nicknaming themselves e-Estonia, the country became, arguably, the most digitally advanced nation in the world. Residents of the country have electronic ID cards, and do things like file tax returns and vote online. Estonia has become a hotbed of tech start-ups (Estonian engineers helped to build the technology behind Skype), and in 2018 the country introduced the world’s first “digital nomad” visa, allowing people who can work from anywhere the chance to live and work in Estonia.

We found Tallinn to be a fascinating place—it has a very well-preserved, yet fairly touristy, Old Town, and some one the best and most creative food we found in the region. As a major cruise port, we found ourselves dodging large crowds during the day, but there were also plenty of places to explore that seemed to be overlooked by the day-trippers.

What To See

Tallinn’s medieval Old Town is the big draw for tourists. This picturesque part of the city is full of cobblestone streets, historic buildings, and great viewpoints. Old Town is divided into two areas—Toompea, a once fortified area of the city on a hilltop, and the Lower Town which was once home to the city’s artisans and merchants. Old Town is incredibly walkable, and we found it most enjoyable in the early morning or the later afternoon after the cruise ships had departed for the day.

At the heart of Lower Town is Town Hall Square, a large cobblestone square surrounded by pastel buildings. We found great views of the square by climbing the steep, narrow stairs to the top of Town Hall Tower (the entrance is right off the square on the north side of the building). The historic St. Olaf Church, built in the 13th century, is also in the Lower Town. The city’s biggest medieval structure, its 124m white spire is a distinctive part of the city skyline (and can also be ascended for city views).

The upper part of Old Town is dominated by towering Alexander Nevsky Cathedral, an onion-domed Russian Orthodox church built at the turn of the 20th century. We personally thought the outside of the building was more impressive than the inside, but did enjoy the solitude we found inside one morning when we went right at the opening hour (it was always mobbed mid-day). Down the block from Alexander Nevsky Cathedral is St. Mary’s Cathedral, also known as the Toomkirik. The whitewashed interior is stark, but the church is full of impressive carved wooden coats of arms from Estonia’s noble families. You can also climb to the top of the church’s tower for great panoramic views. Visitors to the Toompea area of the Old Town can also find great views from the Kohtuotsa and Patkuli viewing platforms. Both are accessible down winding alleys, and not hard to find. We slightly prefered the sweeping views from the Patkuli viewpoint, but they are in close proximity to one another and both are worth a stop.

When the crowds got overwhelming, we retreated to the main branch of the Tallinn City Museum in the Lower Town. Built in a 14th century merchant’s house, the museum covers centuries of Tallinn history with extensive artifacts and informative displays (well labeled in English). We especially enjoyed the top-floor display on life in Tallinn during the Soviet occupation and the build up to Estonia’s independence.

There are two city sights worth visiting for those interested in the Soviet occupation period—the former KGB headquarters on Pagari Street and the Hotel Viru. The former KGB headquarters, in the heart of Old Town, allows visitors to tour some of the KGB prison cells and learn a bit more about one of the more difficult aspects of life in Estonia under Soviet occupation. The area of the building available to tour is modest compared to what you can see at the Corner House in Riga, but the display is well done and worth a quick stop for those interested in this era of history.

The Hotel Viru’s KGB Museum offers a different and lighter perspective on the Soviet occupation period. In the early 1970s, the Soviet Union wanted to enter the growing tourism market and built the Hotel Viru to accommodate foreign visitors to the Estonian capital. The Viru was the only hotel where international tourists were permitted to stay and was designed to ensure that the KGB could keep tabs on all the visitors. From a secret base on the 23rd floor, KGB agents monitored everyone’s comings and goings through bugged telephones, listening devices built into the hotel room walls, and even radio transmitters in the restaurant’s dishes. When the Soviet Union began to crumble, the KGB abandoned the hotel so abruptly that all of their equipment, documents, and even some personal items were left behind, only to be found when the secret floor was discovered several years later.

The KGB listening room at the Hotel Viru

Visits to the 23rd floor are available by guided tour only. While there are only two rooms to visit, we found the hour-long English language tour to be very informative and our guide shared a wealth of fascinating stories. The top floor of the hotel also offers a panoramic view of Tallinn’s Old City. Tickets for a tour must be reserved in advance.

Where to Eat

After traveling through Belarus, Lithuania, and Latvia and eating lots of delicious Eastern European foods (rye breads, beet soup, potato pancakes, etc.) we arrived in Tallinn expecting to find similar foods on the menu. We quickly discovered that Tallinn is home to a very different food scene, drawing from local ingredients like the rest of the Baltic states, but with a much greater Scandinavian influence in the composition and creativity of dishes. This “New Nordic” cuisine could be found all over Tallinn, and it reminded us a lot of the farm-to-tables restaurants we love so much in our home state of Vermont. With forests covering 90% of Estonia and an abundant coastline, Estonian chefs have an multitude of local ingredients with which to work. Menus were littered with the season’s bounty—beets, potatoes, parsnips, mushrooms, pumpkin, berries, and more, plus fish and meats like elk, pork, quail, and duck. Unlike the rest of the region where traditional foods tended to be prepared in much humbler ways, the New Nordic influence we found in Tallinn elevated these ingredients and left us incredibly impressed with the creative and delicious dishes we found. The fantastic food paired well with an interesting selection of local craft beers, including many brewed with Estonian rye. Our dining experiences in the Old Town were so fantastic that we would plan a return trip just for the food!

The most traditional Estonian restaurant we sampled was Vanaema Juures (which means Grandma’s Place). Set in a cozy basement in the Old Town, the small restaurant offered hearty local fare including meat dishes like elk, lamb, and local sausages, along with some nice vegetarian selections. This was the one place we got to sample the traditional kama dessert, a pudding-like mixture of rye, oat, barley, and pea meal mixed with cream and served with fresh berries.

Right next to Vanaema Juures is the more contemporary Von Krahli Aed, offering local ingredients in modern presentations. Part of the appeal for us was that every dish on the menu could be ordered as a meat or vegetarian dish, appealing to both of our palates. Everything was beautifully presented and delicious. We couldn’t resist ordering the dessert simply called “goat”—a combination of goat cheese, goat milk and goat’s milk ice cream—an unusual (and monochromatic!) way to end our meal.

We also had the chance to dine at one of Tallinn’s top restaurants, Rataskaevu 16. We tried to make a reservation when we arrived in town and were told that the restaurant was booked all week. (We discovered this was a trend throughout the city during our time there—availability in the summer was at a premium and we would recommend making reservations for any of the restaurants we dined at.) They sent us around the corner to their other location called Väike Rataskaevu on Niguliste Street​. The second location serves the same menu, which was diverse and delicious. A highlight is that the wait staff takes the time to present each dish with an explanation of the ingredients and preparation. After such a great first meal there, we decided we would try to get a lunch seating at Rataskaevu 16 on our last day in the city, and we lucked out. We were able to get a rare free table as walk-ins, and we were able to have a second round of their fantastic food.

Even with all the fine dining we experienced, we couldn’t help but seek out one much more humble local dessert called kohuke. Mentioned to us by a friend in Latvia, kohuke is found in much of the Baltic region and consists of a block of sweet curd covered in chocolate or a similar hard shell topping—the filling reminded us of cheesecake in both taste and consistency. Popular during Soviet times, they come plain or in favors like berry, caramel, or chocolate. We found some at a gas station convenience store (in the refrigerated section) and knew we had to try it. It ended up becoming one of our favorite snacks during our road trip.

Where to Stay

For our stay in Tallinn, we chose a historic hotel in the heart of Old Town called Hotel Telegraaf. Built in 1878, it served as the home of the Tallinn post office and as a central communication hub for decades. The building was restored and opened as a hotel in 2007. The interior is elegant with nods to the building’s history, but we were disappointed that our room was in a newer wing of the hotel and more modern than what we were expecting. The location was ideal, though—we were right around the corner from Town Hall Square, but the hotel was an oasis of calm despite the masses of tourists in the city during the day.

Getting There and Away

We visited Tallinn as part of our Baltic road trip, so we arrived and departed by car. The medieval Old Town is not very car-friendly, and after our experience of trying to drive into the Old Town of Riga, we opted to look for parking nearby and walk to our hotel. We found affordable overnight parking near the Old Town in the parking garage attached to the Viru Keskus mall and Hotel Viru.

The Tallinn Airport offers many regional flights to other parts of Europe, and many visitors also come to Tallinn on the ferry from Helsinki (a one-way trip takes around two to three hours depending on the boat). We had hoped to travel to Tallinn on the train, however at the time of our visit there were no direct trains to the other Baltic capitals.


Tallinn was a welcome surprise on our Baltic road trip. The city has a very distinctive feel compared to Riga and Vilnius, and there was an obvious sense of embracing history while still being innovative and forward-thinking. We had not anticipated the hoards of cruise ship day-trippers, but found ways to work around the crowds and find sites that were more off the beaten path. We were most pleasantly surprised by the culinary scene, however. The food we ate was creative and modern, yet honoring to the local ingredients prevalent in the region. There were many other restaurants we didn’t get a chance to try, and even more neighborhoods we would like to explore—we are already planning a return visit to this spectacular city on the Baltic Sea!

3 thoughts on “Tallinn: 36 Hours in Estonia’s Medieval Marvel

  1. As always you make the trip and the location so appealing. Big downside with the tour boats–going to be the death of so many locations around the world!!!

    Like

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