Tallinn, Estonia

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On the shores of the Baltic Sea, Tallinn, Estonia’s largest city, is impossibly charming. Northern Europe’s oldest capital—it dates back to the 12th century—is also one of its best preserved, with much of its Old Town constructed when it was a bustling port in the Hanseatic League.

Explore the upper portion on Toompea Hill, where there is an impressive castle and the 19th-century Alexander Nevsky cathedral, a vestige from the Russian Empire, then head to the lower section for churches and merchants’ homes off twisting medieval streets.

Tallinn isn’t, however, simply a historic showpiece. Just a short walk from the UNESCO World Heritage-designated core is a dynamic, future-facing city of glass buildings and trendy restaurants and boutiques catering to the city’s young professionals—as well as visiting travelers.