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.

Masters' Courtyard in Tallinn stands out as a distinctive artisan quarter, featuring more than 10 diverse shops run by local craftsmen and artisans, along with a guesthouse and a chocolate shop.

Situated at the heart of Tallinn's historic old town, this property has a rich history dating back to 1371, having changed ownership and purposes numerous times over the past seven centuries. In 1993, the Master's Courtyard Non-profit Organization was established with the primary goal of restoring and revitalizing this property, which had suffered significant deterioration. Their vision was to transform it into an artisan hub comprising workshops, galleries, and exhibition spaces.

Today, Masters' Courtyard has gained recognition as a popular attraction for both residents and tourists alike. There are 11 distinct shops that exclusively offer products created by local artisans and artists. Some of these shops allow visitors to witness the crafting techniques and even place orders for customized items. On the courtyard's premises, you'll also find the cozy Guesthouse "Villa Hortensia," featuring six rooms equipped with kitchenettes and private bathrooms.

Additionally, there's a well-regarded chocolaterie named Chocolaterie Pierre, renowned for its handcrafted truffles, cakes, and an array of excellent coffee offerings. As you explore the various buildings within the courtyard, you'll soak in the historical ambiance, and during sunny summer evenings, you can enjoy live music in the garden.

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.

Toompea Hill is a limestone hill that sits about 20-30 meters (65 feet-98 feet) above the rest of the city. In Estonian mythology, Toompea is a grave mound erected by Linda for her husband, King Kalev. Linda sat on the grave mound, shed tears, and formed Ulemiste Lake.

Throughout Tallinn's history, the hill has been the site of various forts built to defend the city. Castle Square is the site where Tallinn was founded by the Knights of the Sword in 1229. Today, the spectacular Russian-style Alexander Nevsky Cathedral stands in Castle Square.

Toompea is the center of Estonia's government. Parliament meets in the Toompea Castle, which is topped by the Tall Hermann Tower. Tall Hermann was completed in 1371. Tradition dictates that whichever country flies its flag over Tall Hermann rules Estonia. Each day, the Estonian flag is raised at sunrise while the national anthem plays and lowered at sunset to the tune of My Fatherland is My Love.

In 1684, Toompea had a terrible fire, and most of its buildings were damaged. Because of the fire, Toompea has newer buildings than Lower Town and has a different look.

Toomkirik (Dome Church) was built in the 13th century and survived the brutal 1684 fire. Don't miss the medieval coats of arms in this beautiful example of an Estonian Lutheran Church. Toompea Castle was built on the ruins of a fortress built here during the 13th and 14th centuries. The current castle was completed in 1773 and features a pink Baroque facade.

Why You Should Visit:
Toompea has long been the seat of power for the area. The hilltop site has a long history, gorgeous views of Old Town, and exciting architecture.

Tips:
Check out one of the viewing platforms for a panorama of Old Town below and the Gulf of Finland. The view is breathtaking at sunset.

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.

Saint Mary’s Cathedral is the oldest church in Tallinn. It dates all the way back to 1219, and was built during the time that the Danes conquered Tallinn. The original was built completely of wood. A group of Dominican Monks came in 1229 and started construction of a stone church to replace the old one. A letter sent to Rome in 1233 is the oldest documented note about the church. In 1240, the building was completed. In the same year, it was made into a cathedral and dedicated to the Virgin Mary. The size of the church was expanded in the 14th Century.

The grand old structure was badly damaged in the great fire of 1684. Most of the remaining wooden structure was lost, as well as some of the beautiful woodwork in the chancel. The church was restored and that is why today you see a Baroque style pulpit in the building. The pulpit and the altarpiece were done by the famous Estonian sculptor Christian Ackermann.

The exterior of the church dates from the 15th Century, and the large spire dates from the 1700s. Most of the current furnishings are Baroque in style and also go back to the 17th Century.

There are many famous Estonians buried in the church's cemetery. Among them are Jindrich Matyas Thurn, Samuel Greig and Adam Johann von Krusenstern.

If you are looking for a postcard-perfect picture of Tallinn, head to the Patkuli Viewing Platform. The 157 step stairway begins in Toompark by the Snelli pond. These steep steps were built in 1903. This is the quickest and most straightforward route to reach the top.

The stairs are steep, but there is another easier and more scenic way to access the viewing platform. You can walk through the Danish King's Garden and past the Alexander Nevsky Cathedral to access the Patkuli Viewing Platform. From the top of the viewing platform, you can see Old Town, its walls and towers, the port, and the Gulf of Finland. You'll see picturesque red rooftops, the Town Wall, Saint Olav's Church, and the castle towers.

It might be worth climbing the stairs to this viewing platform twice. Climb in the day for bright views to the horizon. Climb again at dusk when the lights of the city magically twinkle. If you're traveling during the peak summer months, you might want to climb the steps before 10:00 am or after 5:00 pm to avoid crowds.

Kohtuotsa Viewing Point, located in Tallinn, is one of the city's most popular and picturesque viewpoints. Perched on Toompea Hill in the heart of Tallinn's historic Old Town, this viewing platform offers visitors breathtaking panoramic views of the city and its surroundings. It's easily accessible on foot from various parts of the Old Town and is a must-visit attraction for tourists exploring Tallinn's historic center.

The main attraction of Kohtuotsa Viewing Point is the stunning view it provides. From this vantage point, visitors can enjoy a sweeping vista of Tallinn's Old Town, the modern cityscape, and the picturesque Gulf of Finland. It's particularly beautiful at sunrise and sunset when the city is bathed in warm, golden light.

The viewpoint allows you to spot several iconic landmarks of Tallinn, including the medieval walls and towers of the Old Town, Alexander Nevsky Cathedral with its onion domes, and the spires of Saint Olaf's Church. You'll also have a clear view of the bustling city below and the harbor in the distance.

The viewing point features a raised platform with safety railings, which provides a safe and comfortable place to take in the scenery. It's a popular spot for photography, so be sure to bring your camera or smartphone to capture the stunning views.

Kohtuotsa Viewing Point is free to access and is open year-round. The walk to the viewpoint may involve some uphill terrain and steps, but it's generally easy to reach on foot from various parts of the Old Town. It's also conveniently located near other attractions like the Toompea Castle and the Danish King's Garden.

After taking in the views, you can explore the charming streets of Tallinn's Old Town or visit one of the nearby cafes for a coffee or meal. This area is well-known for its cozy and historic dining establishments.

Town Hall Square is a fabulous location to soak up the long and storied history of Tallinn. It's in the center of the Old Town. Markets began opening on this site in the 11th century. Tallinn Town Hall is located in this square. Completed in 1404, it's the oldest Town Hall in Northern Europe.

Other historical buildings surround the square. There is the oldest pharmacy in Europe; it was established in approximately 1415. The pharmacy has a small museum with ancient medical instruments and medicines. The rest of the buildings are painted in attractive pastel colors and were built between the 15th and 17th centuries. Cobblestones throughout the square complete the old-world charm.

In the center of the square, visitors will find a circular stone with a compass rose. The L-shaped stone near the center of the square marks the site where a priest was executed. The priest killed a waitress who had served an overcooked omelet.

During the summer, the square is filled with open-air cafés. Enjoy alfresco dining and people-watching. There are regular outdoor markets held in Town Hall Square. Stalls feature souvenirs and traditional Estonian items.

You will find varied festivals and concerts throughout the year. Tallinn Old Town Days is a week-long festival that takes place at the beginning of summer. During this popular festival, visitors and locals are treated to exhibitions, theater plays, concerts, fairs, and non-stop entertainment.

In winter, the square becomes a winter wonderland with holiday decorations and a massive decorated fir tree. The Brotherhood of the Blackheads first erected a Christmas tree in the square in 1422. This is thought to be the world's first Christmas tree. Visitors can also enjoy a spirited Christmas market.

Why You Should Visit:
Town Hall Square is the oldest town square in Northern Europe and has been the center of Tallinn for eight centuries. Visit historic buildings and enjoy the old-world ambiance. There's no better place to get the feel of the town and nation than Town Hall Square.

Tips:
This square is incredibly festive over the winter holidays. Have a hot toddy, enjoy the holiday lights, shop for gifts, and admire the Christmas tree.

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.