The most essential of the many things to do in Tallinn is an exploration of the Old Town. Its romantic cobblestone streets and ancient towers were once home to tradespeople and artisans, but now house cool cafes and small shops. Climb to the top of Toompea Hill for a guided tour of Toompea Castle, which is currently the seat of Estonia’s parliament. Here you can learn about the history of the forts and strongholds dating back to the 13th century. Toompea Hill boasts panoramic city views and is also home to the Alexander Nevsky Cathedral, an ornate, onion-domed Russian Orthodox church filled with mosaics and glittering icons.

Tap into the contemporary energy of Tallinn at Telliskivi Creative City, a former locomotive repair warehouse that’s now the city’s entrepreneurial and design hub. Here you’ll find an array of fabulously cool places to eat and 25 or so independently run shops. Pick up clothes by local designers, chic leather goods, books, beautifully woven wool textiles, and Estonian beauty products like peat face masks. You can stop for lunch at the perennially popular F-hoone, a high-ceilinged all-day restaurant, and grab a cappuccino or a glass of organic wine at the comfy Reval café. Finish up with one of the hundreds of fantastic cultural events hosted at the space, from photography exhibits to dance performances to flea markets.