Most meaningful encounter: Hanging out with Kadri and exploring the town!

Top tips:

  • Learn about the startups at Garage48 Foundation and Tallinn’s position as a digital city.
  • Soak up the views across the medieval Old Town from the Toompea Castle.
  • Wander through the charismatic streets of the Old Town and shop for Lithuanian amber.

As a thunderstorm raged around me, I sat in my Tallinn hotel watching a documentary about the World Wars and the devastating loss of life. It was shocking to discover just how many people were murdered in the Baltic states and Poland, setting a melancholy tone on my first night in Estonia.

Much like Lithuania, Estonia has a very scarred past. The Swedes, Russians, Germans and Soviets have all taken turns at ruling this Balkan country. Around 25% of the population lost their lives during World War II and it wasn’t until 1994 that the Soviet soldiers finally left.

Arriving into Tallinn from Lithuania, it immediately had a different atmosphere, with a beautifully preserved medieval Old Town. Referred to by the Russians as the “big red castle”, Tallinn’s main attraction is Toompea Castle, which perches atop a limestone hill overlooking the city. Below sprawls the maze of streets that is the Old Town, packed with red-roofed houses and beautiful old churches.

The first time I entered a shop in Tallinn, I noticed that the Estonians are much more commercially-minded than their Lithuanian neighbors. The sales people were more aggressive while at the same time being friendly. Countless shops sold amber stone that comes from Lithuania, although I hadn’t seen the variety of designs available in Tallinn when I had been shopping in Vilnius.

When Tallinn was originally built in 1050, it was a port for trading between Russia and Scandinavia, with its long-established trade history still evident in the commercialism of Estonians today. The blending of Russian and Scandinavian traits also explains the beauty of the Estonian people and their sense of fun. My guide that day Kadri from Gamefounders was both, showing me around the city and sharing a few glasses of wine.

Estonians are not only innovative business developers but they’re fast movers on the technology scene, particularly when you consider their population is only around 1.5 million. Tallinn is home to the Skype headquarters and a number of other startups, with the Garage48 Foundation home to a couple of dozen vying to grow their business internationally. It’s been rated as a Top 10 Digital City and just launched the first ever e-resident program so anyone can become a resident and start a company.

For anyone interested in startups or medieval history, Tallinn ticks both boxes, making it a great destination for business or culture.

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