Winging It On Location – Days 2-3 - Tallinn: A Trendy Old Town, Estonian History and Monopoly Deal

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Winging It On Location – Days 2-3-Tallinn: A Trendy Old Town, Estonian History and Monopoly DealIn this second instalment of my Winging It On Location series from the Baltics, I spend two full days exploring Estonia’s capital beyond the first evening impressions. From avocado toast in one of Tallinn’s trendiest cafés to a deep dive into the country’s Soviet history, this episode blends food, culture, history and the small moments that make a trip memorable.

I wander through the cobbled streets of the Old Town in the sunshine, join a free walking tour to learn about Estonia’s path to independence, and take in panoramic views across the city. The next day I head out to the seaside district of Pirita, visit the Soviet memorials and cemetery, and reflect on how Estonia preserves difficult parts of its past.

There’s also excellent coffee, cardamom buns, goulash in a bread bowl, jazz at Philly Joe’s, and the beginning of a travel obsession that may last the rest of the trip: Monopoly Deal.

If you’re considering a European city break that feels safer, quieter and less crowded than many of the continent’s major capitals, Tallinn might be the perfect choice.

In this episode:Exploring Tallinn’s Old Town, cafés and bakeriesLearning about Estonia’s history on a free walking tourVisiting Soviet memorials and Pirita BeachJazz, wine and final thoughts on Tallinn as a city break

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⏱️ Timestamps00:00 Back in Tallinn and exploring the Old Town in daylight

02:30 Cafés, bakeries and the free walking tour

05:00 Evening food stops and first impressions of Tallinn