Tucked in the northeast corner of Europe, Tallinn is a true hidden gem. Whether you visit in the summer high season or in the wintry cold, like I did, there are countless cool things to do in Estonia’s capital city. For me, two days was the perfect amount of time to get a good feel of Tallinn, but then I move fast. If you want to see the city at a slower pace, then I recommend at least three days.
In any case, no matter how much time you have, be sure to explore outside of the Old Town as well as inside it so as to get a real feel for modern Tallinn. The city is quite compact and walkable, with excellent public transport. It’s super easy to combine a visit to Kalamaja and Telliskivi with a day of exploring the Old Town and still manage to see all of the most important things to see in Tallinn.
Any visit to the Estonian capital would simply not be complete without walking around the UNESCO World Heritage Old Town. Sure, it’s touristy, but it’s for a reason as it’s one of the best preserved medieval cities in all of Europe!
With 500-year-old buildings, streets that transport you straight to a fairytale past, and hidden medieval walkways full of historic houses, the Old Town has more intrigue and history in its tiny nucleus than other cities have in their entire limits.
Walking on the cobblestone streets around the quaint Old Town felt magical with cafe workers dressed in vintage clothing ushering guests into Estonian restaurants. Tallinn’s architecture is truly amazing and you will not want to miss the dozens of photo ops at every twist and turn.
Most visitors enter the Old Town through Viru Gate. The two towers are actually only a small part of what was a much more complex gate system built in the 14th century. Most of the gate was pulled down in the 1880s to make room for traffic, but these two towers remained and have since become a symbol of the town.
There are countless buildings worth seeing in the Old Town. One of my favourites was the apothecary in Town Hall Square, the oldest (and still functioning to this day) pharmacy in Europe. Tallinn town hall pharmacy was first mentioned back in 1422!
Other notable buildings in Tallinn Old Town are St Olaf’s Church (the tallest building in the world, though only for 76 years, until the Eiffel Tower was built), the Dome Church, Alexander Nevsky Cathedral and the Town Hall. St Olaf’s Church is home to a Baptist congregation but its list of former operators includes a far more sinister name – the KGB. During the Soviet times the church’s spire was fitted with powerful radio and surveillance equipment. It was the highest point in Tallinn after all.
The Tallinn town hall is the oldest surviving Town Hall in the Baltic countries and Scandinavia. It was first mentioned in 1322 and by the year 1404, it was finished and got its present looks. The Town Hall square used to be the gathering point for all citizens. Today, the Tallinn town hall serves as a ceremonial building of the city government as well as museum. During the summer months, it’s possible to visit the town hall tower.
If you’re looking for a beautiful panorama, there’s no better area than the scenic overlooks on Toompea Hill. This 10th-century stronghold offers breathtaking views over the city, giving a new perspective to the combination of historic charm and modern culture that thrives within Tallinn.
One of the highlights of the upper town and Toompea Hill is, without a doubt, Alexander Nevsky Cathedral. It can be spotted from the distance and it surely stands out among other churches and cathedrals. This beautiful Orthodox cathedral was built during the tsar times in 1900, when Estonia was part of the Russian Empire.
In a small passage tucked away behind larger buildings, one can find St Catherine’s Passage, housing the traditional artisans of the city. Once home to a convent and the centre of learning within the city, the cobbled streets have seemingly refused to modernise. For this reason, it’s one of the top places to visit in Tallinn’s Old Town. Handicrafts, clothing stores, and more can be found in small shops dotting the alleyway, a perfect stop for souvenir shopping. Unfortunately, there were no artisans anywhere to be seen that day even though it was late morning. Perhaps, it was because I was visiting in winter.
There’s no shortage of adorable coffee shops and cafés located in Tallinn. Besides the obligatory cappuccino I also recommend ordering a sprat sandwich or Kiluvõileib. The Baltic Sea is full of sprats, so it is not a coincidence that this fish can be found in almost every restaurant and shop. There are many dishes made with sprats, but the most popular and simplest is Kiluvõileib, also known as a sprat sandwich. The recipe is simple—dark bread, sprat, boiled egg and some sauce. It might not look attractive, but you can be sure it is delicious.
My host of the apartment I was staying at recommended I eat at the Olde Hansa. It’s a medieval-themed restaurant right in the heart of the Old Town but prices are ridiculously high here and, in any case, I had already gone to a similarly-themed restaurant in Latvia’s capital city Riga. I wouldn’t by any means characterise Olde Hansa as a “must,” but if Tallinn is your only stop in the Baltics, you’re not on a budget and the concept seems like fun to you, you could give the place a whirl.
In my case, I made a beeline for the Peppersack right opposite. This restaurant makes wonderful use of the 15th-century building it calls home. Both the vast main hall and the more intimate rooms further back exude comfy medieval-ness. The menu is European-based, with hearty dishes to satisfy any palate.
Once inside the restaurant, I ordered a squash and parsnip creamy soup with seeds and pork tenderloin with beer-stewed sauerkraut, marinated beetroot, potatoes and mushroom sauce. For dessert, I chose date and nut cream with berry sorbet. I had made a good choice as the food was delicious, so perfectly hearty and filling on a cold day in Tallinn, and the prices were very reasonable.
Estonia is also known for its delicious chocolate! Kalev, the oldest chocolate factory in Estonia, produce chocolate of the highest-quality. They also make very tasty and stylish gifts and souvenirs which you can take back home. At Kalev chocolate shops, you will find a wide selection of traditional Kalev sweets and additional exclusive, handmade candies and gorgeous marzipan figurines.
I also visited Kalamaja, the artsy residential and small business district, and the hipster nucleus of the already-hip city. With gorgeous murals and haphazard graffiti splashed across many of the buildings, Kalamaja is a paradise for lovers of street art and good food.
Tallinn 
Tallinn 
Tallinn 
Tallinn
On my way towards Kalamaja, I made a brief stop at the Balti Jaama Turg or Baltic Station Market. It’s a newly renovated market that offers not only fresh convenience food but also food courts, restaurants, shops and even a gym. Before the renovation, the market was a typical Soviet one with shady sellers and old kiosks; now it is a really modern and popular public space that offers multiple things basically under a single roof. From traditional Estonian products to Taiwanese street food vendors to funky antiques, this market really has something for everyone if you look for it.
Am I over Estonia? I am not. I would love to go back as I did not have time to visit the Seaplane Harbour Museum, Telliskivi Creative City and the KGB Museum. I would also like to get out of Tallinn and explore further afield.
