Day 298: Exploring Medieval Tallinn

Weather Update: Sunshine, High 23°C

Elevation: 12 metres (39 ft)

A Quiet Start

Just another start to the day: I set up, finished yesterday’s blog with photos, and had breakfast of three eggs on toast. It was a beautiful morning with blue skies overhead. I wished Remy a safe trip to Riga before venturing out into streets that seemed unusually empty.

The past few days, cruise ships have brought crowds pouring into the Old Town, and it’s been hard not to bump into them. Today, though, I had space to breathe. No matter which way you walk here, you will eventually come across one of the 26 towers and ramparts still intact, even though the Soviet Union heavily bombed the city during German occupation.

Kohtuotsa Viewing Platform

My first stop was the Kohtuotsa Viewing Platform, situated at the top of Toompea Hill. This is one of Tallinn’s most popular viewpoints, famous for sunrises and sunsets. From here, you can take in sweeping views of Old Town and modern Tallinn side by side.

It’s the kind of spot where you can immediately spot iconic landmarks: the medieval walls and towers, Alexander Nevsky Cathedral, and the spire of St. Olaf’s Church.

Leaving the platform, I walked down a staircase leading to the lower level and quickly stumbled upon Nunna (Nun’s) Tower and Kuldjala (Golden Foot) Tower—an impressive stretch of intact wall with adjoining towers.

Nuns Tower and Kuldjala Tower

About 1.85 km of Tallinn’s city wall has survived, including 26 defensive towers, two intermediate gates, and parts of two front gates. A section here connects the Nun’s Tower, Sauna Tower, and Golden Foot Tower, all dating from the 14th century.

This part of the wall stretches several hundred metres and includes the Monastery Gate. Standing there, I could see Nuns Tower with the gate below, Sauna Tower rising in the middle, and Golden Foot Tower far to the right. Photos give the best sense of the scene, but standing there in person gave me goosebumps—like stepping back in time.

Church of the Holy Spirit

Next, I decided to visit the Church of the Holy Spirit, today used as a Baptist church. It’s tucked close to the city wall, though you have to backtrack and circle to reach it from Old Town.

From the outside, the church looks plain and simple. Inside, however, it’s magnificent. I almost turned away when I saw there was a ticket fee, but after a quick chat with the custodian, I offered to donate instead. He asked me what I wanted to give—I said one euro, expecting to haggle—but he happily accepted. That small coin opened the door to a remarkable interior.

Painted panelling decorated the high cloisters, and I could only imagine how vivid the colours would look if they were ever cleaned. Stained glass windows with 25 individual panels glowed in the afternoon light. Hopefully, my photos will give you a sense of what I saw.

History of the Church

First mentioned in written sources in 1319, the Church of the Holy Spirit may not face east because it was forced to adapt to the surrounding street layout. With its timber interior and hexagonal tower, the bright white building is one of Tallinn’s oldest and finest structures.

The façade holds a clock that has been measuring time since the 17th century. Inside are treasures like a unique altar created by Berndt Notke in the 15th century and a pulpit from 1597.

In medieval times, this was the main sanctuary for commoners. After the Reformation, it became the first church to hold sermons in Estonian instead of German. Johann Koell’s Catechism, published in 1535, is considered the first book in Estonian.

The church has seen many changes—the original wooden ceiling was replaced in 1360 with vaulting and large Gothic windows, and the tower, rebuilt after fires in 1684 and 2002, now stands as both a landmark and survivor.

As I was leaving, I met a young couple debating whether to go in. They were ready to walk away, but I told them it was worth every cent. They took my advice and stepped inside.

St. Olaf’s Church

My next stop was St. Olaf’s Church, or St. Olav’s. Entry to the church is free, but climbing the tower costs 9 euros. I chose to admire the church itself rather than pay for the view—you can see Old Town from so many other points around the city.

Tallinn’s churches are like museums, and its historic buildings are often museums too. If you paid entry fees everywhere, you’d spend hundreds of euros. It’s best to pick and choose carefully.

History of St. Olaf’s

Believed to date back to the 12th century, St. Olaf’s was the centre for Tallinn’s Scandinavian community before Denmark conquered the city in 1219. It was originally a Roman Catholic church but became Lutheran during the Reformation.

By World War II, it had no active congregation, and in 1950, the Soviet regime handed it to the Baptists. From 1944 to 1991, its spire served the KGB as a radio tower and surveillance point. Today, services are still held here, a living reminder of Tallinn’s layered history.

Great Coastal Gate and Fat Margaret

After leaving St. Olaf’s, I followed Google Maps toward the House of the Brotherhood of Black Heads. The app sent me toward the port, which made sense given these were once merchants and traders, but something felt wrong. I paused, reset the map, and realised I was indeed headed the right way.

Along the route, I stumbled across the Great Coastal Gate.

Next to it stands Fat Margaret, a tower built between 1511 and 1530 during the reconstruction of the city’s gate system. With walls 25 metres wide, 20 metres high, and up to 5 metres thick, it was the biggest part of Tallinn’s fortifications. It was built not just to defend the harbour but also to impress visitors arriving by sea. Back then, the shoreline reached right up to the walls, though today it is several kilometres away.

Later, Fat Margaret was used as a gunpowder store, then a prison. Today it remains one of the most striking defensive structures in the city.

Tallinn Walls

A few days ago at the Bastion Passages, I learned how Tallinn’s walls were lowered and reinforced with grassy mounds to resist cannon fire. On my way toward the port, I came across another great example—an impressive reminder of how the city adapted to changing warfare.

A Wrong Turn and a Lucky Break

Still determined to find the Brotherhood’s house, I pressed on. Google Maps eventually told me I had “arrived,” but all I saw was a food-and-drink area. Feeling frustrated, I ducked into a nearby casino to escape the sun. Beer there was only 4 euros—much cheaper than the 6–10 euros you’ll pay in Old Town—so I sat down, cooled off, and caught up on some work.

I finally subscribed to GPSmyCity, an app I’d tried on and off. For $12.95 USD a year, it gives detailed walking guides, and within minutes, I realised my destination had been only a short walk from where I’d started. My detour had cost me 4 km. Lesson learned!

House of the Brotherhood of Black Heads

At last, I reached the House of the Brotherhood of Black Heads. A tour group blocked my photo at first, but I patiently waited for them to move on.

Historically, this was the headquarters of a guild for unmarried foreign merchants, shipowners, and traders in Livonia (modern-day Estonia and Latvia). The Brotherhood fled to Germany during the Soviet occupation in 1940, but their house remains one of the city’s gems.

The building reflects Dutch Renaissance style and consists of three connected structures. Inside are four halls and several rooms used for events. The White Hall was built in the early 1530s but remodelled between 1909 and 1911. St. Olaf’s Guild Hall, purchased by the Brotherhood in 1919, retains early 15th-century interior features.

Catherine’s Alley

From there, I walked into Catherine’s Alley, once known as Monk’s Alley. This winding passage runs from Vene Street past the Dominican Monastery to Müürivahe Street.

St. Catherine’s Church, which gave the alley its name, was built over 700 years ago. The southern side of the alley is lined with 15th–17th-century buildings, restored in 1995. Old tombstones lean against the walls, remnants of the Dominican Monastery and St. Catherine’s Cemetery.

Handicraft workshops line the alley today—ceramics, hats, glasswork—all made on-site. It’s a place where history and living craft meet.

Hellemann Tower and City Wall

At the end of the alley stands Hellemann Tower, connected by a nearly 200-metre-long defensive wall to Munkadetagune Tower. Climbing its steep stairs brings you to an attic that opens into a viewing platform.

The tower is thought to be named after Helle Holleman, a local citizen. In medieval times, its location near the Viru Gate was strategic for defence.

Here, I met a German couple who had visited New Zealand, and we struck up a warm conversation—a reminder of how travel connects strangers in unexpected ways.

Winding Down

By now it was late in the day, and I headed back to the hostel. Dinner was pasta with stewed red peppers and tuna—simple but filling after so many kilometres.

Tallinn has been long and full of discoveries, but I hope this post inspires you, which is the whole aim of Inspire Seniors Travel. This isn’t just for older travellers but for anyone with an appetite for culture and adventure.

I’d also love your input for a small hostel poll:

What’s one thing you love about hostels?

What’s one thing you dislike?

For me:

I love hostels that have an atmosphere where people sit together and share experiences.

I dislike it when guests make too much noise while others are sleeping. I always pack the night before so I can leave quietly in the morning—it’s just common courtesy.

You can reach me at: a.matthews2453@gmail.com

I’ve also booked my ferry to Finland for Monday, so a new adventure awaits.

Peace,

Andrew