Start your tour at Viru Gate, the iconic entry to Tallinn’s Old Town, a UNESCO World Heritage site, with its twin medieval towers evoking a fairy-tale charm. Admire the flower stalls and the cobblestone street ahead. From here, stroll west along Viru tänav, a lively street lined with shops and cafés, capturing Tallinn’s medieval yet vibrant atmosphere.
After about 10 minutes, stop at Olde Hansa (Vana Turg 1), a medieval-themed restaurant near Raekoja plats (Town Hall Square), offering a quick lunch of hearty Estonian dishes like elk soup or wild boar with sauerkraut, reasonably priced for its historic ambience, no reservations needed for smaller groups, but arrive early to avoid crowds. The candlelit, rustic interior feels like stepping into a 15th-century Hanseatic scene.
Continue to Raekoja plats, the heart of the Old Town, where the Gothic Town Hall and its arcaded façade dominate. Wander the colourful square, surrounded by pastel-hued merchant houses. Head north to St. Catherine’s Passage, a narrow alley with artisan workshops and stone arches, offering a glimpse of Tallinn’s medieval crafts heritage.
Proceed to Alexander Nevsky Cathedral, a striking Russian Orthodox church atop Toompea Hill, with golden onion domes and intricate mosaics. Pop in for a quick look at its ornate interior (free entry). Nearby, explore Toompea Castle, home to Estonia’s parliament, with its pink baroque façade. A quick stroll around the Danish King’s Garden offers views of the city’s medieval walls.
Loop east to St. Olaf’s Church (Lai 50), a 12th-century landmark with a towering spire. If time allows, climb the tower for a 20-minute panoramic view (small fee). From here, wander south along Pikk tänav, a historic street lined with guildhalls, to the Great Guild Hall, now housing the Estonian History Museum. A brief 20-minute visit (small fee) showcases Tallinn’s Hanseatic past.
Head back towards Raekoja plats and stop at Maiasmokk Café (Pikk 16), Tallinn’s oldest café since 1864, for a hot chocolate or coffee with a marzipan pastry, a local speciality, no bookings needed, but arrive promptly to enjoy its vintage charm.
End your tour at Freedom Square (Vabaduse väljak), a modern plaza with the Victory Column and views of the Old Town’s spires. For a final treat, visit Kohvik Must Puudel (Müürivahe 20), a quirky, retro café for a coffee or a slice of kringel (Estonian cinnamon bread), soaking up Tallinn’s eclectic vibe. Alternatively, relax at Kehrwieder Chocolaterie (Saiakang 1), near Raekoja plats, for a creamy hot chocolate, watching the medieval city’s lively street life unfold.This 3-4 km route captures Tallinn’s medieval allure, Baltic cuisine, and cosy charm, perfect for a four-hour stroll. Wear comfortable shoes for the cobbled Old Town streets and bring a warm jacket for Tallinn’s often chilly, breezy weather
