This city has some of the most stunning sights in the Western Hemisphere, because this was where the Columbus family settled down and the Spanish crown established an empire. In 1503, Columbus’ son, Diego Colon, built what is now the oldest stone house in the New World—Casa del Cordon and today there’s free admission for visitors.
In 1517, Diego traded up to the rather extravagant, 22-room Alcazar de Colon, and you’d be hard pressed to find anything else like it on this side of the Atlantic.
Basilica Catedral Metropolitana Santa Maria de la Encarnacion, the oldest cathedral in the New World, is (of course) in Santo Domingo, as are the ramparts of Fortaleza Oazma, Iglesia y Convento Dominico (a still-functioning church-and-convent) and Monasterio de San Francisco, all of which hail from the early-1500s. But it’s not just public and monumental buildings: in Zona Colonial you can stroll through an entire 12-block neighborhood from the days of the Spanish Empire. No wonder this city is a UNESCO World Heritage Site.
At the same time, Santo Domingo is a modern, living city, with hundreds of restaurants, clubs, cafes, concerts, and casinos. For of-the-moment cuisine in historic settings, dine at La Briciola and La Residence. For after-dinner gaming try the Diamonte or Majestic casino. There’s also dancing at Diamonte, but for something completely different, visit Guacara Taina, a weekend-only dance club in a series of caves once used by the Taina Indians. Where to stay? Brad Pitt and Robert de Niro have opted for chic Hostal Nicolas de Ovando, a hip hostelry whose location couldn’t be better—it’s right at the Zona Colonial.