Tallinn Old Town

A town hall pharmacy that has been dispensing medicines on the same corner since at least 1422 – possibly since the late 14th century – tells you something about how Tallinn treats continuity. Raeapteek, at the base of the Gothic town hall on Town Hall Square, may be the oldest continuously operating pharmacy in Europe. It is still a pharmacy. You can walk in, look at the original fittings, and buy paracetamol. This is the thing about Tallinn’s Old Town: it did not become a museum district. It remained a place where people live, work, and run businesses, which makes it more interesting than the average preserved medieval quarter.

Tallinn’s Old Town (Vanalinn) is one of the best-preserved medieval city centres in Northern Europe. The UNESCO listing in 1997 covers roughly 1.5 square kilometres of walled town retaining most of its 13th and 14th-century street pattern, two distinct levels – Toompea hill above and the merchant town below – and a working population. Twenty-six of the original 46 towers survive, along with significant stretches of the limestone wall.

Toompea (Upper Town)

Toompea is the limestone plateau forming the upper half of Old Town, historically the seat of power for whichever authority controlled Tallinn. The current pink baroque facade of Toompea Castle houses the Estonian parliament (Riigikogu), which has met there since 1920 – a detail that stops you short when you think about the building’s age.

Alexander Nevsky Cathedral (completed 1900) is a Russian Orthodox church built during the Tsarist period, positioned prominently on Toompea in a way that was intended to make a political statement about Russian authority. The onion domes are visible from most of the lower town. It remains an active cathedral.

The Dome Church (Toomkirik) is the oldest church in Estonia, with parts of the current building dating to the 13th century. The interior carries coats of arms of Estonian noble families – austere in a way that feels genuinely old rather than decorative.

Two viewing platforms on the Toompea walls – Kohtuotsa and Patkuli – give broad views north across the lower town’s orange roofline toward the port and bay. Patkuli is consistently less crowded and the better vantage point, particularly in the late afternoon light.

Lower Town

The lower town is where the medieval merchant city functioned. The street pattern between the main gate at Viru and Raekoja Plats (Town Hall Square) is essentially unchanged from the 14th century.

St Olav’s Church has a slender Gothic spire reaching 124 metres that was, during various periods between the 16th and 19th centuries, the tallest building in the world. The observation platform below the spire is open in summer, accessible via a steep internal staircase that takes about 20 minutes each way; the view from the top is the best elevated perspective of the city.

Katariina Kaik is a narrow 16th-century lane off Vene Street with workshops of local craftspeople operating in former convent buildings – weavers, jewellers, ceramicists. It is one of those places where the physical space is more interesting than the products for sale.

Where to Eat

Rataskaevu 16 in the lower town has built a consistent reputation for solid, non-touristy Estonian food in a medieval cellar setting. Book ahead in summer; July walk-ins are an optimistic bet.

Lee Brasserie, included in the Michelin Guide, stands out for seasonal Estonian ingredients and solid technique. The lunch menu is genuinely good value compared to dinner prices.

Avoid the restaurants immediately on Town Hall Square; they price for location rather than quality. Walking one or two blocks in any direction reliably gets you better food at better prices – a universal rule in tourist-heavy European old towns, and Tallinn is no exception.

Where to Stay

Hotels within the walls occupy converted medieval or 19th-century buildings; rooms are often small and irregular, which is either atmospheric or annoying depending on your travelling style. Hotel Telegraaf on Vene Street, in a former 19th-century telegraph office, is more polished than the average Old Town option.

Getting There

Tallinn is served by flights from most major European cities. The airport is 4 km from Old Town; a tram line runs directly to the old city edge. The ferry from Helsinki takes 3.5 hours; the overnight from Stockholm is a standard route. The Helsinki ferry is fast enough that day trips are a regular occurrence – resist this if you want to actually understand the city rather than count it as visited.