Our Wandering Chapter

We’ve added practical details and tips in the NOTES section at the end of this post.

An overnight sail from Stockholm to Tallinn feels like stepping from one world into another. As the Baltic Queen, operated by Silja Line, set sail from Stockholm Värtahamnen at 17:30 CET, we settled in for the overnight voyage. The ship offered everything for a comfortable journey from cozy cabins, dining, and live music to duty-free shopping, but the real highlight was the view. Watching the autumn-hued islands of the Stockholm archipelago drifting by felt like travelling through a moving painting.

For another Baltic chapter, read about our trip to Helsinki, the Finnish capital just across the sea.

Arrival in Tallinn

We arrived in Tallinn in the morning at 10:45 (Estonian time). From the cruise port, the walk to the Old Town takes around 25-30 minutes, passing landmarks like the Stolting Tower and the Fat Margaret Tower, home to the Estonian Maritime Museum. Both landmarks stand as quiet sentinels, guiding visitors toward the medieval heart of the city.

Our first stop was St. Olaf’s Church, one of Tallinn’s most striking landmarks. The narrow spiral staircase of 258 steps leads up to a viewing platform with sweeping views over the Old Town and beyond. From above, red-tiled roofs, cobblestone lanes, and pastel facades stretch out like a storybook scene merging into the modern skyline. A visit to St. Olaf’s Church offers both a glimpse of Tallinn’s history and one of its best panoramas. While the church is free to enter, entry to the tower (open April to October) requires a small fee.

Wandering the Old Town

After the climb, we spent the rest of the day wandering through the Old Town’s cobbled streets, soaking in its medieval charm. The crisp autumn air carried a hint of wood smoke, and golden leaves framed every view. At Raekoja plats (Town Hall Square), a fair was underway: colourful stalls, crafts, and people in traditional costumes turned the square into a lively scene straight out of the Middle Ages.

Around the square, we admired the Tallinn Town Hall, one of the oldest in Northern Europe, and the historic Town Hall Pharmacy (Raeapteek), which has been serving customers since the 15th century.

As we continued uphill, we passed the Eduard Vilde monument, the Nõelasilma Gate, and the striking Alexander Nevsky Cathedral, its onion domes gleaming against the autumn sky.

Beside Toompea Hill, the Danish King’s Garden offered one of the most atmospheric corners of the city, with its trio of monk statues and views of St. Nicholas Church below evoking Tallinn’s layered history and legends.

Our final stop before returning to the port was the Viru Gate, its twin towers standing like sentinels at the entrance to the Old Town’s bustling shopping streets. Just outside the gate, we lingered for a moment at the flower market (Mercado de Flores), a vibrant stretch lined with colourful blooms, a fragrant farewell to this medieval city.

On our next visit to the Estonian capital, Tallinn had transformed into a winter wonderland, its red roofs and cobbled lanes glistening with snow. Read more in our winter post on Tallinn.