1. Cuba

Distance from NYC: 3 hours and 35 minutes

Average hotel room cost: $124 per night

Cuba's unique architecture, '50s-era Chevy taxicabs, and sandy beaches have been just out of reach for American tourists until recently. Years of US embargo have left the Caribbean island undeveloped compared to its more modern neighbors, so there aren't too many fancy hotels on the island yet. There are, however, a number of local paradores and Airbnb rentals available for travelers.