Cortina d'Ampezzo, Italy
This stunning region of Italy's Dolomite Mountains—featuring peaks over 9,000 feet above sea level—was the site of the 1956 Winter Olympics and has always attracted a swanky European crowd, including movie stars and royals. But strict zoning has kept the area true to its surprisingly Teutonic roots, and you'll see white-timber houses that look as if they were transplanted out of a fairy tale. The popular Cortina d'Ampezzo ski resort offers a seven-day Dolomiti Superski pass, which gives you access to all the area's slopes for about $40 a day, and booking your trip now can nab you reasonable airfare and hotel rates for this tony enclave.
Get There: Round-trip flights from New York to Rome on Alitalia start at $1,071.
Stay: Domina Home Alaska is centrally located in Cortina d'Ampezzo and offers complimentary breakfast and a fitness center (39 Largo delle Poste, Cortina d'Ampezzo, Italy, dominahome.it/en, doubles from $150).