Founded when Columbus and his clan landed on "Hispanola," Santo Domingo is considered the oldest city of the New World. Now with 500 years of documented history under its belt, UNESCO declared the colonial district a World Heritage Site.

A day trip is a must, but a few days are better to explore the Euro-Caribbean charm and museums of the city. And whether you're a lady or not, be sure to stroll down the oldest constructed street in the Americas, the Calle Des Dames.