Day 1: Medieval city & bohemian Kalamaja
The Tallinn Old Town is a medieval UNESCO World Heritage Site with especially well preserved city walls. Winding streets radiate out from the Town Hall Square, an impressive stone structure built in 1404. For the best bird's eye view, ascend St. Olav's church spire, one of the world's tallest buildings when it was constructed in the 16th century. Climb Toompea hill to the upper city to see the pink parliament, ornate Alexander Nevsky orthodox cathedral and yet more stunning photo opportunities of the city and sea. In the afternoon, head to the Kalamaja district, named for its history as a fishermen's neighbourhood. Only a short walk from the Old Town, you'll find vibrant, wooden, two-story buildings housing cafés, design shops and some of Tallinn's best restaurants. Check out local goods at the Balti Jaam Market and try one of the eateries at Telliskivi Creative City for dinner.