Friday Evening — Arrive & Walk the Old Town
Drop your bags and head straight into Vanalinn, Tallinn's old town. Start at Town Hall Square (Raekoja Plats), the medieval heart of the city, ringed by merchant houses and dominated by the Gothic Town Hall. The square is at its best in the early evening — café terraces filling up, the octagonal tower catching the last light.
From there, wander the Lower Town's alleys towards St Olaf's Church — for a brief spell in the 16th century, the tallest building in the world. You don't need to climb it tonight; save the tower for daylight. Instead, find dinner in one of the old town's cellar restaurants (many occupy genuine 14th- and 15th-century merchant vaults), then walk up Pikk jalg (Long Leg Street) towards Toompea for a first look at the hilltop silhouette lit up against the sky.
Saturday — Toompea, the Lower Town & Kalamaja
Morning: climb Toompea Hill properly. The Alexander Nevsky Cathedral, an onion-domed Russian Orthodox church built in 1900, sits in striking contrast to the Gothic streets below it. Toompea Castle next door now houses the Estonian parliament. Walk to the viewing platforms on the hill's edge for the best panorama over the Lower Town's red roofs and church spires — Kohtuotsa and Patkuli platforms both deliver, so do both if you have twenty minutes to spare.
Late morning: descend back into the Lower Town and climb St Olaf's Church tower — 258 steps up a narrow spiral staircase, but the view over the old town rooftops and the Baltic horizon is the best in the city. Go before midday to beat the queue.
Lunch: grab something quick near the Balti Jaama Turg (Baltic Station Market), which also gives you an excuse to walk towards Kalamaja.
Afternoon: spend it in Kalamaja, the wooden-house district northwest of the old town. This is Tallinn's hippest neighbourhood — independent cafés, natural wine bars, and Telliskivi Creative City, a former industrial complex turned hub of design studios, vintage shops, and street art. The Saturday flea market at Telliskivi is worth timing your visit around.
Evening: dinner in Kalamaja, then a drink at Põhjala Brewery's taproom or Pudel — both are local craft beer institutions, a world away from the old town's tourist-facing bars.
Sunday — Seaplane Harbour & Departure
Morning: the Seaplane Harbour (Lennusadam), Estonia's maritime museum, housed in a restored Art Nouveau seaplane hangar on the Noblessner waterfront. The centrepiece is the submarine Lembit (1936), which you can walk through in full. Give it at least ninety minutes — it's one of the best maritime museums in Europe and rarely crowded.
If time allows before your flight or ferry: walk back through the old town one last time via Vene Street, quieter than the main tourist routes, and stop at the oldest pharmacy in continuous operation in Europe (since 1422), on the corner of Town Hall Square.
Head to the airport or ferry terminal — Tallinn Airport is a 15-minute bus ride from the centre, and the Helsinki ferry terminal is walkable from the old town.