Cortina d'Ampezzo, Italy

With a population of just 5,546, Cortina d'Ampezzo is an upscale ski resort town that transforms into a bustling tourist hub in the winter, when its population can swell to 40,000. Winters here are long, frigid, and frequently snowy, and bureaucracy is a persistent headache as the town navigates its location between Veneto and Trentino-Alto Adige/Südtirol. But for those seeking a luxurious alpine getaway with world-class skiing, designer boutiques, and a jet-set social scene, Cortina d'Ampezzo could be the perfect destination.