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 travelers 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.