Tallinn has the most complete medieval old town in Northern Europe, on the UNESCO list since 1997. It survived because the city was never comprehensively rebuilt and because the Soviet period, whatever else it did, left the walls alone.
Upper and lower town
The city splits in two, and the division is historical rather than decorative. Toompea, the upper town on its limestone hill, was where the nobility and the ruling power sat — today it holds the Estonian parliament in the pink baroque castle, and the Alexander Nevsky Cathedral, an onion-domed Russian Orthodox church built in 1900 as a deliberate statement of imperial presence, and still not universally loved locally.
The lower town was the merchants' city, the Hanseatic trading centre. The two were separated by gates that were locked at night — the Long Leg and Short Leg passages still connect them.
Raekoja plats and the town hall
The Town Hall Square has been the centre of the city for eight centuries. The Raekoda, completed in 1404, is the only surviving Gothic town hall in Northern Europe, topped by Old Thomas, the weathervane guard who has stood there since 1530 and is the city's mascot.
On the square stands the Raeapteek, a pharmacy trading continuously since at least 1422 — one of the oldest in Europe still operating in the same building. Its small museum room displays some of the remedies it once sold, which are not for the squeamish.
The walls and the viewpoints
Around 1.9 kilometres of the original wall survive, with twenty of the original forty-six towers. Several can be climbed, and the walk along Hellemann tower gives the clearest sense of the defences.
The two essential viewpoints are on Toompea: Kohtuotsa, looking over the red roofs to the modern city and the sea, and Patkuli, angled towards the towers and the port. Both are free and both are busy in summer.
Beyond the walls
Kadriorg is the baroque palace and park Peter the Great built for Catherine in 1718, now holding a foreign art museum, with the excellent KUMU — the Estonian national art museum — at the far end of the park.
Telliskivi Creative City and the Rotermann Quarter are the industrial districts converted into studios, restaurants and shops, and they are where the city's contemporary life actually happens. Kalamaja, the old fishermen's quarter of wooden houses, is the most pleasant area to walk in.
Practical
The old town is compact and entirely walkable, with cobbles that punish unsuitable shoes. It is at its worst in the middle of the day in summer, when cruise passengers arrive in numbers, and at its best early in the morning or after nine in the evening. Most museums close on Mondays.