At one point in time, there were a total of 45 towers built into the walls that protected Tallinn. Twenty-six of those still remain. Two of the best preserved of the bunch are called Viru Gate. The gate dates from the 14th Century, as do most of the towers, and sits at the entrance way into the Old Town.

Today the two towers are quite lovely, having been covered in ivy over the years. It gives a gentle look to Viru Street. When you first enter the Old Town through the gate, it makes you feel as though you have stepped back in time.

The towers used to be the fore gates to the city, and a larger set was built a little further in, which were held up by a set of square towers. Most of the gate was pulled down in 1880, in order to make room for more street traffic. Since that time, though, the two towers have become a symbol for the Tallinn Old Town, which used to be the most fortified city in all of Europe back in the day.

Parts of Tallinn's City Wall have stood since the 13th century. This wall was one of the strongest defense systems in Northern Europe. At its peak, the wall had 45 wall and gate towers and was over two and a quarter kilometers long. Today, 26 towers and less than two kilometers of the wall remain.

The Hellemann Tower was built in the early 15th century. It was named after a resident who owned land nearby and was built to protect Viru Gate. Helleman Tower has three levels and a three quarter circle layout. The 11 meters (33 feet) tall first floor was used as an ammunition room. The tower has also been used as a prison.

Today, Helleman Tower houses an art gallery and offers wonderful views of Town Hall and the rest of Tallinn.

Visitors can also walk along a 200 meter (656 feet) section of the City Wall. This is the longest portion of the wall that is open to visitors. It's surprisingly high up; visitors can see the city streets below and be transported back through the centuries.

The Dominican Monastery Claustrum is located in the Old Town of Tallinn, not very far from the Viru Gates, which are the official entrance into this part of the city. The Monastery here was first formed in 1246, during a time period when the city was a thriving.

From a historical perspective, the building is one of the most important in all of Tallinn. The clausure holds the most important rooms in the old building, and they were used for many purposes during the years. During the 14th and 15th Century, the meetings of the leadership of the Hariju and Virumaa Knighthoods took place here. The Old Capital Hall used to be here also.

One of the first libraries in Tallinn was also located inside the Monastery. In addition to being able to see the old library, you can visit the old sacristy, vestry, and dormitories used by the monks and leaders of the city.

There is an extensive collection of medieval and Renaissance art and artifacts to be seen. You will especially want to check out the stone carvings, particularly those on some of the old tombstones. The relief of the angel, set in a triangle, is also quite stunning and was designed by Arendt Passer. He was a famous stone mason who did other work in the area, like the Pontus de la Gardie in the famous Tallinn Cathedral.

Just to the south of the monastery lies a narrow alley that is known as Catherine’s Passage. The wall here was from the original Monastery. There is a series of craft shops where you can watch artisans at work, just as in the days gone by.

If you want to get a chance to really glimpse what life was like in the Old Town of Tallinn, you will want to visit Saint Catherine’s Passage. It is located just a short distance from the Town Hall.

The old passage connects Vene and Muurivahe Streets in town. On the northern end of the passage you will find the remnants of Saint Catherine’s Dominican Monastery Church, which is one of the oldest church in the city. In fact, the passage derives its name from the church. Many people like checking out the old tombstones that are an integral part of the sanctuary there. Many famous Estonians are buried at Saint Catherine’s cemetery.

The southern end of the passage will take you past some of the best artisan shops in Tallinn. You can watch the artists at work. It’s one of the best places to get a memento of your visit to Tallinn. The whole passage is a nice morning’s hike for the exercise alone. If you want to stop for a moment, you will want to get a cup of coffee at one of the quaint little cafes that are scattered down the passage.

Saint Olav’s Church is one of the oldest churches in the city of Tallinn. It was built during the 1100s, and has been the center for religious life for the Scandinavian community of the city since then. Many people that attend here can trace their heritage back to when Denmark conquered Tallinn in 1219. The church is dedicated to King Olaf II of Norway though. The oldest surviving records that refer to the church are from 1267.

There is an old legend that the builder of the church, who was also named Olaf, fell to his death from the towers of the church. It adds mystery to this place. There is a painting depicting the event in the Chapel.

Sadly, the building was damaged during the 1300s, and had to be heavily rebuilt. In the 1500s, the tower of the chapel was raised to 159 meters in the air. It has been struck by lightning many times, but the tower really has a utilitarian function: it is a seaside landmark for naval vessels. From 1549 until 1625, before the tower was burned from a lightning strike, it was the tallest structure in the known world.

During the Soviet era, the KGB used the church’s spire as a radio tower and surveillance point. Today the building now houses a Baptist church.

The tower's viewing platform offers tourists one of the best views of Tallinn, and is open to the public from April through November of each year.

The Nunna, Sauna, and Kuldjala Towers are three of the remaining 26 towers that surround the Old Town of Tallinn. In the late 14th century, a massive project was started to build a fortified wall around the city to protect against invaders. By the 16th Century, the walls were raised to sixteen meters high with a thickness of 3 to 4 meters. This made it possible to defend against canon fire. During the 16th century, Tallinn was one of the most fortified cities in the entire world. The wall stretched 4 kilometers around old Tallinn.

These three towers are among the few that are still open to the general public. Visitors can come and walk through all three. In addition, there are some connection paths that are adjacent to the historic standing walls. It gives you a real sense of what the old town was like. Climbing the towers also gives you a great view of the city. You can imagine what it was like to be a guard on the towers. Admission is free.

Tallinn Old Town, known as "Tallinna vanalinn" in Estonian, is the historical heart of Tallinn. Renowned for its well-preserved medieval and Hanseatic architecture, this area is a living testimony to the city's rich history. Spanning 113 hectares with a buffer zone of 2,253 hectares, the Old Town is characterized by its 13th-century city plan, which remains remarkably intact.

The Old Town has a history of prosperity and turmoil. Most buildings date back to the 13th-16th centuries, reflecting its medieval importance. However, WWII caused significant damage. Between 1941-1944, Soviet air raids, during the German occupation of Estonia, destroyed about 10% of Old Town buildings, leaving 20,000 homeless and many casualties.

Despite this turbulent history, Tallinn Old Town stands today as Northern Europe's best-preserved medieval city. Its Gothic spires, winding cobblestone streets, and enchanting architecture attract visitors worldwide. The area was once a hub for wealthy merchants from Germany, Denmark, and other regions. Now, it is a vibrant center with restaurants, bars, museums, and galleries, offering a blend of historical ambiance and modern vitality.

The Old Town's unique charm lies in its ability to maintain its medieval and Hanseatic structure completely. Recognized for its historical value and well-preserved state, it was inscribed as a UNESCO World Heritage Site in 1997. The city's layout includes original cobblestone streets lined with medieval churches, grand merchant houses, barns, and warehouses, many dating back to the Middle Ages.

Visitors to Tallinn Old Town often describe it as mystical, mesmerizing, and addictive. Spending a day wandering through its streets offers an immersive experience in an authentic medieval milieu, revealing why it holds such a special place in the annals of world heritage sites.

The Alexander Nevsky Cathedral is an orthodox cathedral in the Tallinn Old Town. It was built to a design by Mikhail Preobrazhensky in a typical Russian Revival style between 1894 and 1900, during the period when the country was part of the Russian Empire. The Alexander Nevsky Cathedral is Tallinn's largest and grandest orthodox cupola cathedral. It is dedicated to Saint Alexander Nevsky who in 1242 won the Battle of the Ice on Lake Peipus, in the territorial waters of present-day Estonia. The late Russian patriarch, Alexis II, started his priestly ministry in the church.

The Alexander Nevsky Cathedral crowns the Toompea Hill, the political center of Estonia. The cathedral was built during the period of late 19th century Russification and was so disliked by many Estonians as a symbol of oppression that the Estonian authorities scheduled the cathedral for demolition in 1924, but the decision was never implemented due to lack of funds and the building's massive construction. As the USSR was officially non-religious, many churches including this cathedral were left to decline. The church has been meticulously restored since Estonia regained independence from the Soviet Union in 1991.

The phrase “Kiek in de Kok” derives from German, meaning "Peep into the Kitchen". Kiek in de Kök was an old artillery tower. Occupants of the tower used to be able to peek down into the kitchens of nearby homes, hence the name.

The tower was built in 1475 as part of the impressive fortifications that used to surround the town. It stands an impressive 38 meters high, and is made with walls that are 4 meters thick, which were designed to stand up against canon fire. Today you can still see old cannon balls that are embedded into the walls of the tower that date all the way back to the 16th century.

The old tower has been modified many times during its lifetime. In the 17th Century new gun holes were made at the top of the tower. The structure fell out of use by 1760. For a while, it became a repository for archives and was used briefly as apartments.

Today, the tower is a museum for the town’s fortification system with displays showing how the city's system of walls and towers developed through the centuries as well as other facets of life in old Tallinn. From the museum, one can also enter the Bastion tunnels, dating back to the 17th to 18th centuries, are an integral part of the city’s defense system.

Freedom Square was built to commemorate the soldiers who were killed during the Estonian War of Independence. This war was part of the Russian Civil War that occurred between WWI and WWII. The war actually took place from November 1918 through February of 1920. During the struggle, 4,000 people were killed and another 14,000 were wounded.

The idea for a tribute started in 1939, but Estonia was swept into WWII shortly after the independence was declared. After WWII Estonia was part of Soviet Union and it wasn’t until 1991 that the country was again independent. During the Soviet times, this plaza was called Victory Square. This beautiful area has been redesigned to reflect the freedom of the Estonian people and to pay tribute to its fallen citizens.

On the west side of the square is the Victory Column. It was completed and opened in June 2009. The column is surrounded by 143 plates of glass and is topped by the Cross of Liberty. The Victory Column serves as a memorial for those who fell during the Estonian War of Independence. On the east side of the square is the lovely Saint John’s church.

Saint Nicholas Church is a basilica style church located in the Old Town part of Tallinn. It is fairly large in size, having three full aisles down the sanctuary. It is an Orthodox community of faith, which was started by merchants from Westphalia during the 13th Century, though a good deal of the structure is a couple of hundred years younger, as improvements were made during the years.

A fair bit of damage was done to the building by Soviet bombing during the Second World War, and that is partly why the local community turned it into a museum. It houses much of the surviving sacred artwork of Tallinn that survived the Protestant riots there in 1524.

Among the things to see are pieces like the Gothic altarpiece done by Herman rode of Lubeck. They feature events in the life of Saint Nicholas and Saint George. The Crucifixion scene that is located to the left of the altar is also quite stunning, though the artist is unknown. The Altar of the Blackheads is also very beautiful.

A side chapel holds the remains of Duke Charles-Eugene de Croy. It used to be a local attraction, primarily because the structure had preserved the body so well. Authorities finally buried the body in 1897 to put an end to the almost freakish attraction people had to the corpse.

There is also a beautiful old organ here that gets played about every Saturday and Sunday evening.

Tallinn Town Hall is the oldest and only preserved Gothic-style city hall in North Europe. In 2005, the Town Hall was awarded second prize for conservation of Architectural Heritage. Parts of the town hall date to the 13th century. The Town Hall was completed in 1404 and was the center of the town's government for almost 700 years, until 1970. Throughout the centuries, several additions, renovations, and architectural changes have been made.

Tallinn Town Hall was built with limestone. Traditional clay tiles adorn the exterior, which features a 64 meter (210 feet) tall spire that's visible from all over town. Gargoyles decorate the main facade. The Town Hall has an arcade formed with nine arcs and eight pillars. In inclement weather, merchants could gather under the shelter of the arcade. Criminals would be chained to one of the pillars so that townspeople could mock them.

The Town Hall's interior features attractive Gothic arches and works of art spanning the history of Tallinn. Benches were crafted in the 14th and 15th centuries. The largest hall in Town Hall is the Citizens Hall. It can hold up to 100 people and is often used for musical performances.

The Council Chamber features intricate wood carvings dating to 1375. Copies of 16th-century tapestries hang on interior walls. The original tapestries are on display in the Tallinn City Museum.

The Old Thomas weather vane is one of the town's most famous landmarks. The weather vane depicts a soldier who protects the city. Old Thomas was originally placed in 1530. Today, a copy stands on top of the town hall's spire, while the 1530 original is on display in the town hall's basement.

Tallinn regularly hosts concerts and receptions in this historic building. For a great view of the city, bring your camera and climb the tower.