Tallinn Old Town Historical Guided Walking Tour

Town Hall Square and the Old Town Hall Pharmacy

Raekoja plats, the Town Hall Square, has been the marketplace of Tallinn since the 13th century and is still the heart of the lower town, ringed by merchants' houses and café terraces. On its south side stands the Town Hall, finished in 1404 and the only surviving Gothic town hall in Northern Europe, with an entrance arcade, dragon-headed drainpipes and the weather vane of Old Thomas, the city's guardian, on its 64-metre tower. In the north-east corner the Town Hall Pharmacy has sold medicines from the same premises since 1422, which makes it one of the oldest pharmacies in Europe still in business.

The tour begins and ends here. Our guide meets you under the Town Hall clock, uses the square to explain how the Hanseatic merchants ran the city, and finishes at the pharmacy, where you can step inside afterwards to see the small exhibition of old remedies. In December the square hosts the Christmas market, and in summer the terraces stay busy until late under the northern light.

St Nicholas Church, Freedom Square and Kiek in de Kök

From the square the route passes St Nicholas Church, Niguliste, a 13th-century merchants' church that was badly damaged in 1944 and rebuilt as a museum of medieval art, best known for a 15th-century Dance of Death painting and its silver collection. A few minutes on, the Old Town opens onto Freedom Square, the modern civic plaza beneath Toompea hill, where the glass Victory Column of the War of Independence rises beside the Harju hill gardens. Above it stands Kiek in de Kök, the cannon tower built in 1475 with walls four metres thick; its name means 'peep into the kitchen', because the soldiers on top could look into the chimneys of the houses below.

Each of these stops takes five to ten minutes, with photo time at the tower, which is still marked by cannonballs lodged in its wall. The tower and the bastion tunnels beneath it form a museum you can visit afterwards; on the tour you see it from outside before climbing to the upper town.

Toompea Castle and the Alexander Nevsky Cathedral

Toompea is the limestone hill where Tallinn began, and its castle has been the seat of whoever ruled Estonia since the Danish king built a stone fortress here in the 13th century. Today the pink baroque wing added in 1773 houses the Riigikogu, the Estonian Parliament, while behind it the medieval Tall Hermann tower rises 45 metres; the national flag is raised on its top at sunrise every day. Directly opposite stands the Alexander Nevsky Cathedral, the Russian Orthodox church completed in 1900 with onion domes, mosaics and the largest set of bells in Tallinn, built when Estonia was part of the Russian Empire.

The two buildings face each other as symbols of two eras, and our guide spends about seven minutes at each explaining why. The cathedral interior is open outside service times and entry costs nothing, so you can go in briefly if the group timing allows; photography inside is not permitted. Tours inside Parliament need separate advance booking and are not part of this walk.

St Mary's Cathedral and the viewing platforms

A short walk along Toom-Kooli street brings you to St Mary's Cathedral, the Dome Church, the oldest church on the Estonian mainland, founded in the 13th century and rebuilt after the fire of 1684; its walls are lined with the carved coats of arms of noble families and the tombs of admirals and generals. Beyond it lie the two viewpoints that every Tallinn viewing platforms search is about: Kohtuotsa, with its sweep across the red roofs, church spires and the sea, and Patkuli, which looks straight along the city wall with its towers to St Olaf's Church and the harbour.

The guide gives about ten minutes at Kohtuotsa and eight at Patkuli, enough for photos from the best angles; Kohtuotsa is the one with the painted wall that travellers photograph. The Dome Church interior and its tower are not included, but the church is open most days until the late afternoon if you want to return.

Danish King's Garden, Lühike jalg and Pikk street

The way back down leads through the Danish King's Garden, the terrace below the castle wall where, according to the legend told on every Tallinn history tour, the Danish flag fell from the sky during the battle of 1219; bronze figures of faceless monks now stand among the trees. From here you descend Lühike jalg, the Short Leg, a steep stepped lane that passes through a gate tower of 1456 into the lower town. Pikk, the Long Street, then runs past the Great Guild Hall of 1410, which houses the Estonian History Museum, the ornate House of the Brotherhood of Blackheads and the medieval merchants' houses known as the Three Sisters.

These final stops take two to five minutes each, and the guide uses them to explain how the two towns, noble Toompea and merchant Tallinn, lived side by side behind separate gates that were locked at night. The walk ends back on Town Hall Square after about two hours.