Viru Gate is part of the ancient defense walls during the 14th century. A total of eight gates were built a few centuries later. When the entrance of the Old Town extended, some gates were taken down so the Viru Gate could connect the Old Market and Kadriorg Palace. Today, it is one of the busiest points in Tallinn where numerous events and festivals take place. A line of flower shops leading up to the Gate also showcases many restaurants, cafés and more landmarks.

St. Catherine’s Passage was previously referred to as Monk’s Alley since it used to cross the Dominican monastery. Believed to have been built more than 700 years ago, this charming Medieval passage is home to several local shops that sell handicrafts and souvenirs today. The south side of the alley is where 15h-17th century constructions can be admired.

Tallinn Old Town is action-packed with travelers, locals, medieval buildings, live music, restaurants, bars, cafés…and more. As the oldest part of Tallinn, Old Town is symbolic of a city plan from the 13th century. During WWII, Tallinn experienced aerial bombing by the Soviet air force when the city was under German occupation from 1941-1944. The most damage was done on March 9th, 1944 when over 1,000 bombs destroyed 10% of Old Town’s buildings then created fires that killed locals and left 20,000+ people homeless.

Raekoja plats is the Town Hall Square situated in the middle of Tallinn Old Town. Just as mentioned above, there are numerous restaurants, bars and cafés that encircle the square. Markets, exhibitions are also held occasionally. Try to find the Town Hall Pharmacy (Raeapteek) where one of the oldest pharmacies in Europe is remains open to the public. A Christmas Tree has been celebrated here since 1441, marking the Tallinn Christmas tree display more than 580 years old.

Today’s Estonian History Museum is housed inside the Great Guild Hall which is more than 600 years old with an ancient theater and wine cellar. Since the 14th century, the Great Guild was for artisans and merchants to host events within the walls of classic medieval Estonian architecture. It was also Russian Count Anatoli Orlov-Davydov’s summer residence for holidays. At the present-day museum, there’s a permanent exhibition called, “My Free Country” which explains 100 years of the Republic Estonia.

Balti Jaam Market is one of the best places to shop in Tallinn as it includes 300 vendors over three floors that cover both the interior and exterior spaces. At the entrance, there are several supermarkets, a gym, large halls for fish, meat, vegetables and dining. There’s a wide variety of organic and natural products being sold while the upper floors are various shops featuring Estonian handicrafts, goods, textiles, even vintage shops.

Telliskivi Creative City is a newly artistic center near the Balti Jaama Turg market, and at the former Baltic Railway factory. The entire area covers over 10 buildings and celebrates Tallin’s art world displayed through art galleries, theaters, restaurants as well as more than 30 shops. In addition, Fotografiska Tallinn is a photo art center which highlights the works by local artists. The museum’s restaurant is renowned for its sustainability implementation awarded with a green Michelin star as it’s led by top chef Peeter Pihel.

St. Olaf’s Church was built during the 12th century and was the epicenter of Tallinn’s Scandinavian community before Denmark occupied Tallinn in 1219. The name came from King Olaf II of Norway, at one point, this was the tallest building in the world from 1549 to 1625. During Soviet’s occupation of Tallinn, the KGB used this church as a radio tower and point of surveillance.

One of the most popular museums in Tallinn is the Estonian Maritime Museum which illustrates Estonia’s vibrant history of navigation and ships. Situated at Seaplane Harbor, the museum contains 200 items that range from the Lembit submarine to the Suur Tõll ice breaker and Short 184 seaplane. Visitors can also study the remains of the oldest ship discovered in Estonia.

Estonian Museum of Applied Art and Design is made for art fanatics and takes place in a former granary built in 1683-1695. The museum displays works of Estonian textiles, ceramics, jewelries and artworks from the 20th century to now. There are different levels that feature over 18,000 museum items from Estonian collections of applied art, design and photography.

This is the remaining first wall wrapping Tallinn, called the “Margaret Wall” named after Margaret Sambiria – the Queen of Denmark – who commissioned the construction of the wall. It is less than 16 feet (5 meters) tall. This part of the wall is the reason why Tallinn Old Town became a World Heritage Site. During the 14th century, citizens were required to complete guard duty by wearing armor in case invaders attacked the city.

In Tallinn Old Town, you’ll stroll down Voorimehe Street which means “Coachman.” In 1813, it was named Kleine-Rittergasse which means “Small Knight Street” since it was the place where horsemen stood near Town Hall Square. Today, it’s one of the oldest and most charming alleys in the city where vinyl shops, chocolaterie, cafés reside.

One of the largest museums in Tallinn is Kumu Art Museum, which is also one of the biggest art museums in Northern Europe. Kumu stands for kunsti muuseum meaning “museum of art.” The main exhibition features Estonian art from the 18th century, works from the occupation period from 1940-1991, Socialist realism and Nonconformist art. Notable artists highlighted in the museum are: Carl Timoleon von Neff, Oscar Hoffmann, Ants Laikmaa, Julia Hagen-Schwarz, Oskar Kallis, Konrad Mägi, Jaan Koort, Henn Roode, and Johannes Greenberg.

Next to Kumu Museum is Kadriorg Park which dates back to 1718 when Peter the Great commissioned the redesign of Fonnenthal Summer Manor. Some of the most beautiful parts of the park are the Swan Pond, and the Japanese Garden. The entire park encompasses 70 hectares, it makes a beautiful walk after a visit at the museum.

The Alexander Nevsky Cathedral is situated across the Toompea Castle. Built during the Russian Empire, the cathedral showcases the typical Russian Revival style from late 19th century and is dedicated to the grand prince of Kiev, then later Saint Alexander Nevsky. Since USSR was technically non-religious, most churches were left to decay, but after the end of Soviet occupation of Estonia in 1991, the church was restored.

THE chocolate brand in Estonia is Kalev with its wide selection of flavors and textures. The biggest collection of Kalev candies is its flagship shop in Tallinn: Kalev Rotermanni kvartal šokolaadipood near the KGB Museum. Make sure to stock up on marzipans which are confections made from sugar, honey and ground almonds.

Inside Hotel Viru is the KGB Museum. The hotel was built in 1970s by the Soviets, while few people were ever permitted to the top floor since they were referred to as “technical rooms,” hence many Estonians believed that the building was made in concrete and microphones. Once the KGB left Tallinn in early 1990s, the “technical room” was discovered to be full of espionage equipment. Now, everything has been left as it was with a sign on the door that says, “there’s nothing here” in both English and Estonian which was the answer to those who asked what was behind the door. Guided tours must be reserved ahead of time.