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After hundreds of years as the elite Black Sea playground of czars and nobles, Yalta was made a proletarian vacation resort by decree of Vladimir Lenin in 1920. This meant it was one of the only desirable holiday choices for most Russian vacationers; due to fear of defection to the West, trips abroad were allowed for only the most trusted party members.

The most famous architectural legacy from the city’s lavish patrician past is nearby Swallow’s Nest. Baron von Steinheil’s faux-medieval folly, constructed in 1912 atop a 130-foot cliff, was named for its perch-like position, which offers a tremendous view of the sea. The building itself is a striking sight, looking something like a fairytale castle.

While the area’s many other dachas, or vacation homes, cannot hope to rival Swallow’s Nest for sheer whimsy, many are much more extravagant in size, including Massandra Palace, a faux-French chateau occupied by both Czar Alexander III and Josef Stalin, and Livadia Palace, where Stalin, Churchill and Roosevelt held the famous Yalta Conference to redraw Europe’s postwar boundaries in 1945.

Language: Ukranian     Currency: Hryvnia (UAH)