Day 1 — The Old Town & Toompea Hill
Start in the Lower Town at Town Hall Square (Raekoja Plats), the medieval core of Tallinn, framed by 15th-century merchant houses and the Gothic Town Hall. Climb the Town Hall tower for the first proper view of the old town rooftops.
Spend the late morning wandering the Lower Town's lanes — Katariina käik (St Catherine's Passage), a narrow medieval alley lined with craft workshops, is one of the most atmospheric corners of the city. Have lunch in one of the old town's cellar restaurants, many set in genuine medieval merchant vaults.
Afternoon: climb Toompea Hill via Pikk jalg or Lühike jalg (the Long Leg and Short Leg streets that connect the Lower and Upper Towns). The Alexander Nevsky Cathedral, an onion-domed Orthodox church built in 1900 by the Russian Empire, sits incongruously and beautifully against the Gothic surroundings. Toompea Castle behind it houses the Estonian parliament. Walk to the Kohtuotsa and Patkuli viewing platforms for panoramas over the Lower Town and the Baltic.
Evening: climb St Olaf's Church tower before dinner if you haven't yet — for a period in the 16th century it was the tallest building in the world, and the views are unmatched. Dinner back in the Lower Town, then a walk through the old town after dark, when the crowds thin and the cobblestones and floodlit towers feel genuinely medieval.
Day 2 — Kalamaja, Telliskivi & the Seaplane Harbour
Leave the old town behind and walk northwest into Kalamaja, Tallinn's wooden-house district. Formerly a working-class neighbourhood, it's now the city's creative and culinary centre. Start at the Balti Jaama Turg (Baltic Station Market) for breakfast — excellent smoked fish, black bread, and local produce stalls.
Spend the late morning and early afternoon at Telliskivi Creative City, a former industrial complex of brick factory buildings converted into design studios, independent shops, and restaurants. If it's a Saturday, the flea market here is one of the best in the Baltics.
Afternoon: walk further north to Noblessner, the former submarine factory district on the waterfront, now developing into a design and dining quarter. The Seaplane Harbour (Lennusadam) is here — Estonia's maritime museum, set in a restored Art Nouveau seaplane hangar, with the 1936 submarine Lembit as its centrepiece. Budget ninety minutes.
Evening: dinner in Kalamaja, then Põhjala Brewery's taproom or Pudel for Tallinn's craft beer scene — a genuinely local alternative to the old town's tourist bars.
Day 3 — Kadriorg Park, KUMU & Final Wanders
Morning: walk or tram east to Kadriorg, a baroque palace and park complex built by Peter the Great for Catherine I. The KUMU art museum at the park's entrance is the finest art museum in the Baltic states — a strong collection spanning Estonian art from the 18th century to the present. Kadriorg Palace itself houses a smaller collection of foreign art and is worth a shorter visit.
Spend an hour walking the park itself — formal gardens, ponds, and tree-lined avenues that are beautiful in any season. The walk continues to Pirita Beach if you want to extend it, about thirty minutes further on foot.
Afternoon: head back towards the centre. If you haven't yet, this is the time for Toompea's viewing platforms at a quieter hour, or a slower walk through the Lower Town's less-visited streets like Vene and Sauna.
Final evening: a proper Estonian dinner — elk stew, wild boar, or smoked fish on black bread — at somewhere like Rataskaevu 16 or Leib Resto. Tallinn's restaurant scene has become one of the more interesting in Northern Europe, and it's considerably cheaper than Helsinki or Stockholm just across the water.