Beach lovers flock to the idyllic coasts of Punta Cana and Semana, but many of them make it a point to avoid the island’s bustling capital city of old Santo Domingo. It has a rep for having a gritty stretch or two, so I was surprised to find a breezy colonial town that’s chock full of old world charm (it's actually the oldest European city in the New World.) Tucked along the historic quarters of Zona Colonial are long leafy boulevards, grand European-style squares like the Parque Colon, elegant restaurants, churches dating back to the 1500s, and quaint little shops. It has a few boutique hotel options, too—go for the ideally located Hostal Nicolas de Ovando , which is housed in a former 16th-century Spanish estate. I felt as completely at home sitting around its pool overlooking the Caribbean as I did strolling around the city’s main streets—which were safe to walk even at night.