Old Town

The medieval jewel of Estonia, Tallinn’s Old Town (vanalinn) is without a doubt the country’s most fascinating locality. Picking your way along the narrow, cobbled streets is like strolling into the 15th century – an effect amplified by restaurant staff and others dressed in period garb (don't let the trainers peeping out the bottom puncture your illusion). You’ll pass the ornate stone facades of Hanseatic merchants' houses, wander into hidden medieval courtyards, and find footworn stone stairways leading to sweeping views of the red-roofed city. It’s staggeringly popular with tourists, but manages to remain largely unspoilt: while most historic buildings have helpful bilingual plaques, pleasingly few have been turned into pizza restaurants.

Of course, being so popular comes with its downsides. In summer as many as six giant cruise ships can descend at a time, disgorging their human cargo in slow-moving, flag-following phalanxes that can bring foot traffic to a complete halt. If you’re travelling on such a ship, it’s worth noting that Old Town is within walking distance of the harbour; you’ll have a much better time if you dodge the organized tours and follow your own path. For everyone else, rest assured that most of the boats steam off again in the afternoon, leaving the streets relatively clear by 5pm.

Toompea

Lording it over the lower part of Old Town is the ancient hilltop citadel of Toompea. In German times this was the preserve of the feudal nobility, literally looking down on the traders and lesser beings below. It's now almost completely given over to government buildings, churches, embassies and shops selling amber knick-knacks and fridge magnets, and is correspondingly quieter than the teeming streets below.

Kalamaja

Immediately northwest of Old Town, this enclave of tumbledown wooden houses and decommissioned factories has swiftly transitioned into one of Tallinn's most interesting neighbourhoods. The grim reputation bestowed by its industrial past and the notorious Paterei Prison made this part of town undesirable up until the early 21st century.

Once these were gone, the clapboard houses, tree-lined streets and low costs began to attract people back. Major road projects and the opening of an impressive museum at Lennusadam are only the most visible elements of a revolution started by local hipsters establishing cafes and bars in abandoned warehouses and rickety storefronts. Sadly, much of the area's distinctive weatherboard housing is being torn down to build modern apartments. Kalamaja was half building site, half suburb at the time of research.

Kadriorg & Maarjamäe

Kadriorg, just to the east of central Tallinn, is blessed with wide parklands and attractions such Kadriorg Art Museum, housed in a baroque palace. From here the coastal road Pirita tee curves northeast alongside Tallinn Bay through Maarjamäe – home to a palace, museums and a war memorial – to Pirita. The coastal path is popular with joggers, cyclists and skaters, offering particularly fine sunset views towards Old Town. From the centre, buses 5 and 34A pass through Maarjamäe while tram 3 goes to Kadriorg.

Pirita

Just past Maarjamäe the Pirita River enters Tallinn Bay and the city's favourite beach begins to unfurl. The area’s other claim to fame was as the base for the sailing events of the 1980 Moscow Olympics; international regattas are still held here.

Buses 1A, 8, 34A and 38 all run between the city centre and Pirita.

Kloostrimetsa

Literally 'the convent's forest', this leafy nook spreads out along the north bank of the Pirita River, containing the Botanic Garden and TV Tower. Buses 34A and 38 from the city head here via Pirita Beach.

Haabersti

The westernmost district of Tallinn is home to over 43,400 people, although the population only started to intensify following the completion of the Little Flower Hill (Väike-Õismäe) development in the 1970s. This intriguing example of Soviet town planning features a giant oval ring of immense apartment blocks gathered around an ornamental lake. Haabersti includes the seaside sub-district of Rocca al Mare, home to the Open-Air Museum and Estonia's second-largest shopping mall, the Rocca al Mare Keskus. Buses 42 and 43 head out here from the centre.

Soviet Keepsakes

Nothing says ‘former Soviet’ quite like a brutalist public building, and Tallinn has two that are difficult to miss, both designed by local architect Raine Karp.

  • Linnahall Built for the 1980 Moscow Olympics and originally christened the Lenin Palace of Culture and Sport, Linnahall conceals a vast concert arena within its crumbling, much-graffitied concrete hulk. It’s fair to say that the city doesn’t know quite what to do with it. The ziggurat-like structure has heritage protection but it has decayed considerably since closing its doors in 2009 and it acts as a colossal barricade between Old Town and the harbour.
  • Estonian National Library Like some dour, grey-stone fortress, the National Library squats indomitably on a broad block south of the centre. While construction commenced in 1985, the library's 1993 completion makes it an ironic early entry in the list of independent Estonia's public buildings. The interior, and the frequent exhibitions are worth the time if you have it.