Tallinn
The Alexander Nevsky Cathedral on Toompea Hill was built by the Tsarist Russian government in 1900, positioned on the hilltop to assert Russian imperial authority over the city below. Many Estonians have been trying to demolish or relocate it since independence was restored in 1991, and it remains precisely where it was built, which is why the views from the viewing platforms around it feel slightly complicated if you know the history. It is also genuinely beautiful inside, which complicates things further.
The Old Town
Tallinn has one of the best-preserved medieval old towns in northern Europe: the walled city covers about 113 hectares, 26 defence towers still stand, and the Gothic townhouses and medieval street plan survived the 20th century largely intact through a combination of geography and Soviet policies that prioritised keeping the historic centre nominally functional rather than clearing it for socialist development.
Raekoja Plats (Town Hall Square) is the central point: the 15th-century Gothic town hall on one side, merchant houses on the others. The Medieval Pharmacy on the square has been a working pharmacy, with changes of ownership, for over 600 years.
Toompea Hill (the upper town) has the parliament building (pink neoclassical), the cathedral (complicated history, see above), and three viewpoints over the lower town and the bay beyond. The standard photographs are taken from Patkuli and Kohtuotsa viewing platforms.
The Dominican Monastery Cloister on Vene Street in the lower old town is a 13th-century ruin converted into a cultural space with occasional summer concerts. Often quieter than the main tourist streets.
Eating
NOA on the coastal road north of the centre has a serious reputation for Nordic-influenced cooking at around EUR 35 to 45 per main course; worth booking for a special dinner.
The Balti Jaama Turg (Baltic Station Market) food hall has local producers selling open-faced sandwiches, smoked fish, and traditional pastries at EUR 3 to 8 per item. This is the most straightforward way to eat local food without a formal restaurant. The Telliskivi Creative City district west of the railway station has a younger local crowd and better outdoor drinking in summer.
Estonian food proper: rye bread, smoked fish, blood sausage, and roast pork, with pickled vegetables prominent throughout. The style is northern European in the way that Finnish and Latvian food is northern European; it is not dramatic but it is honest and, at its best, very good.
Getting There
Tallinn Airport is 4 kilometres from the centre; taxis cost around EUR 10 to 15. Direct flights from Helsinki (35 minutes), Stockholm, and various European cities. The Helsinki to Tallinn ferry takes 2 to 2.5 hours; Tallink and Viking Line run multiple crossings daily and it is a comfortable, reasonably priced alternative to flying from Finland.
Tallinn is extremely compact. Almost every tourist sight is within walking distance of the old town. The old town on summer weekends can be chaotic with stag and hen groups from Helsinki and elsewhere; the Kalamaja neighbourhood west of the station and the areas north of the Dominican Monastery have a more local character on the same days.