Day 1: Tallinn in One Day
Old Town: Toompea Hill
Start at Toompea Hill, the upper old town where the Estonian parliament, Alexander Nevsky Cathedral (free, stunning Orthodox interior), and Toompea Castle sit. Walk to Kohtuotsa viewing platform for the iconic Tallinn panorama: red rooftops, medieval spires, and the Baltic Sea beyond. Then the lesser-known Patkuli viewpoint for a different angle. Descend the Long Leg (Pikk Jalg) lane to the lower old town.
Lower Old Town & Town Hall Square
Explore the lower old town. Raekoja plats (Town Hall Square) is surrounded by medieval buildings and the 15th-century Gothic Town Hall (tower climb €5). Walk Viru Street through the medieval gate towers. Visit the Holy Spirit Church (€2) for its beautiful painted clock. Lunch at Kompressor on Rataskaevu for enormous savoury and sweet pancakes (€5–8), a Tallinn institution for budget travellers since the 1990s.
Telliskivi & Estonian Dinner
Walk to Telliskivi Creative City, a former Soviet industrial complex now housing craft breweries, design shops, street food, and galleries. Dinner at F-hoone for modern Estonian cuisine in a converted factory (mains €10–16). Try the Baltic herring, wild boar, or elk if available. Then explore Telliskivi's bars: Pudel for craft beer, or Sveta Baar for cocktails in a converted Soviet-era space.