Day 1 — The Lower Town & Town Hall Square
Start at Town Hall Square (Raekoja Plats), the medieval core of Tallinn, ringed by merchant houses and the Gothic Town Hall. Climb the tower for your first view over the old town. Spend the morning wandering the Lower Town's lanes — Katariina käik, a narrow medieval passage of craft workshops, is a highlight.
Afternoon: climb St Olaf's Church tower — briefly the tallest building in the world in the 16th century — for the best panorama in the city. Dinner in one of the old town's cellar restaurants, set in genuine medieval merchant vaults.
Day 2 — Toompea Hill & the Upper Town
Climb Toompea Hill via Pikk jalg or Lühike jalg. The Alexander Nevsky Cathedral, an onion-domed Orthodox cathedral built in 1900 as a statement of Russian imperial power, contrasts sharply with the Gothic streets below. Toompea Castle next door houses the Estonian parliament.
Walk to both the Kohtuotsa and Patkuli viewing platforms for the full panorama over the Lower Town's red rooftops. Spend the afternoon exploring Toompea's quieter streets, then descend back into the Lower Town via a different route to see the old town from a new angle. Evening: a walk along the city walls near Tornide väljak (Tower Square), where several of Tallinn's original defensive towers still stand.
Day 3 — Kalamaja & Telliskivi Creative City
Spend the day in Kalamaja, Tallinn's wooden-house district and creative heart. Breakfast at the Balti Jaama Turg (Baltic Station Market) — smoked fish, black bread, and local produce.
Telliskivi Creative City, a former industrial complex turned hub of design studios, independent shops, and restaurants, takes up most of the day comfortably. If it's a weekend, the flea market is excellent. In the afternoon, walk north to Noblessner and the Seaplane Harbour (Lennusadam) — Estonia's maritime museum in a restored Art Nouveau seaplane hangar, centred on the 1936 submarine Lembit.
Evening: Põhjala Brewery's taproom or Pudel in Kalamaja for the local craft beer scene.
Day 4 — Kadriorg Park & KUMU
Walk or tram east to Kadriorg, the baroque palace and park complex built by Peter the Great. KUMU, at the park entrance, is the finest art museum in the Baltic states, with a strong collection of Estonian art. Kadriorg Palace houses a smaller foreign art collection.
Spend a couple of hours walking the park itself, then continue on foot to Pirita Beach, about thirty minutes further, for a look at Tallinn's seaside side and the marina. Afternoon: head back towards the centre for a slower walk through the old town's less-touristed streets. Dinner somewhere serving proper Estonian food — elk, wild boar, or smoked fish on black bread.
Day 5 — Lahemaa National Park Day Trip
Lahemaa is Estonia's largest national park, about 70km east of Tallinn — a landscape of coastal cliffs, boulder fields, dense forest, fishing villages, and grand manor houses largely unchanged since the Soviet era. It's best reached by hire car or an organised day tour from Tallinn.
The Viru bog trail, a wooden boardwalk through a raised peat bog, is the park's signature walk — meditative, otherworldly, and manageable in under two hours. Combine it with a stop at one of the restored manor houses, such as Palmse or Sagadi, and a walk along the boulder-strewn coastline near Käsmu, a former sea captains' village known as the "Captains' Village."
Return to Tallinn by early evening for a final dinner in the old town or Kalamaja, depending on which side of the city you preferred.