Tallinn 3 Day Itinerary

Begin on Toompea Hill — the upper city. Visit Toompea Castle (now the Estonian Parliament), the domed Alexander Nevsky Cathedral and the Lutheran Dome Church (Toomkirik). Walk to the Patkuli and Kohtuotsa viewpoints for sweeping views across the red-roofed Lower Old Town and Tallinn Bay.

Descend into the Lower Old Town via the medieval Pikk jalg (Long Leg) and Lühike jalg (Short Leg) gates. Walk along Pikk tänav, the main merchant street, past the Great Guild Hall and St. Olaf's Church — once the tallest building in the world. Stroll to Town Hall Square (Raekoja plats) and climb the Town Hall tower for additional views.

Dinner in the Old Town — Olde Hansa is a theatrical medieval restaurant serving boar, smoked meats and mulled wine in period costume (book ahead). For something more modern, head to the streets just outside the Old Town walls around Telliskivi for a local bar or bistro.

Take Bolt or Tram 1/3 to Kadriorg Park, built by Peter the Great in the 18th century. Visit the baroque Kadriorg Palace (now the Art Museum of Estonia — Foreign Art) and stroll the manicured gardens. The adjacent Kumu Art Museum is the largest in the Baltic states and houses 700 years of Estonian art.

Head to the Song Festival Grounds (Lauluvälják) — the vast outdoor stage where 300,000 Estonians gathered during the 1989 Singing Revolution, which peacefully restored independence. Walk toward Pirita beach for sea air and views of the ruined Pirita Convent (1407).

Spend the evening in Kalamaja, Tallinn's coolest neighbourhood. Balti Jaam Market (inside a converted railway station) has local food stalls, vintage stalls and Estonian craft products. End the night in one of the wood-panelled craft beer bars or natural wine spots nearby.

Visit the Vabamu Museum of Occupations and Freedom — a powerful, design-forward museum covering the Soviet occupation of Estonia between 1940 and 1991. Allow 2 hours. Alternatively, if you skipped Kumu yesterday, this is your morning for it.

Final wander through the Old Town. Pick up gifts along Katariina käik (Catherine's Passage), a cobblestone alley lined with local craft workshops selling ceramics, knitwear, leather and linen — all made in Estonia. The Estonian Design House on Pikk is also excellent for quality local souvenirs.

Tallinn Airport (TLL) is just 4km from the city centre — a Bolt or Bus 2 ride of around 15 minutes. Allow 2 hours before international departure.