"Don’t miss this Gothic Renaissance palace in the Zona Colonial, built between 1510 and 1514 for Christopher Columbus’s eldest son, Diego Colón (governor of the colony and viceroy of the Indies), and his wife, María de Toledo (niece of King Ferdinand ofSpain). Unfortunately, Francis Drake and his band of pirates pillaged the place in 1586, setting fire to the third floor on their way out. What’s left today is a believable re-creation of the original palace—minus one floor—where visiting conquistadores Balboa, Cortés, Pizarro, and Velázquez planned expeditions in grand rooms and plotted to conquer other lands. Visitors can take a solid audio tour of 22 restored rooms, including the viceroy’s waiting room and a ballroom with a crystal chandelier."

"At the top of Calle Las Damas—where María de Toledo (the niece of King Ferdinand of Spain) and her ladies in waiting strolled in fine dresses every afternoon—you’ll find the former Spanish Governor’s Royal Court, made up of the governor’s palace, the treasury, and the courts of law. Built in 1508, the three stone buildings were joined in 1520 and now serve as a cultural history museum, detailing the story of the Dominican Republic from the colonial period through the days of slavery and up to the country’s first independence from Spain in 1821. Highlights include models of Columbus’s three ships and a large map showcasing his four major voyages; portraits of other Spanish explorers and the pirate Francis Drake; treasures from sunken galleons; and ceramic artifacts made by the Taino, the indigenous Indians who occupied the island when Columbus first arrived."

"Just 31 miles east of Santo Domingo, the small fishing village of Guayacanes boasts an uncrowded white-sand beach with gentle surf and plenty of shallow water. A lush backdrop and tall coconut palms offer some shady spots, and umbrellas and chairs are available for rent. When hunger strikes, head to one of the surrounding food shacks or restaurants for a lunch of fried fish, rice, beans, and plantains, all washed down with an ice-cold Presidente."

"Just east of Guayacanes, this six-mile stretch of sand is a favorite of beach bums, with calm waters at one end of the cove and big waves at the other. Busier than Playa Guayacanes, Juan Dolio also offers more food and drink options, plus glass-bottom boat rides and parasailing. For an authentic slice of Dominican life, stop by on Sunday, when local families come to picnic and swim in the warm Caribbean water."

"Built between 1503 and 1508, this Gothic Renaissance relic with Moorish arches was the first hospital in the New World. Named for the patron saint of cures, it was designed in the shape of a Latin cross—the center nave was used for worship and the two lateral sections housed patients. While some walls were torn down in 1911 to avoid collapse, the resulting ruins are still staggeringly beautiful, revealing a story of pirate attacks, hurricanes, earthquakes, and revolution. Visit on Sunday night, when there’s live music, merengue, and salsa dancing in front of the ruins."

"One block down from the oldest cathedral in the New World, this former colonial home on Plazoleta Padre Billini is the place to go at least once, whether for the hearty tapas, affordable tasting menu, expertly prepared cocktails, all-you-can-eat Sunday brunch with unlimited mimosas, or live music and DJs most nights. Here, it’s all about leisurely meals and lively ambience, from the long bar and charming courtyard to the outdoor tables on the square. For a fun night out, attend a tasting at next-door wine shop Cava Billini, then buy a bottle for dinner at Lulú—there’s only a small corkage fee."

"Mesón de Bari You could easily pass by this two-story, 16th-century blue house in the Zona Colonial without realizing there’s a restaurant inside, but step through the red door and you’ll find brightly colored walls covered with paintings for sale by local artists, charming brick arches, and an intimate dining room with coffered ceilings, crystal chandeliers, and white tablecloths. Mesón de Bari specializes in traditional Dominican cuisine, from spicy sausages, stewed crab, and empanadas to goat stew, Creole-style fillet of beef, and steamed fish. There’s also a long bar downstairs, and live music on occasion."

"Experience living history at this charming European brasserie, housed in a space that’s thought to have been the first tavern in the Americas. Opened in 1505 by a Dutch pirate, Pata de Hierro was a favorite hangout of buccaneers on Plaza España, facing the Alcazar de Colón. Since then, not a single change has been made to the interior’s original brick arches or stone walls, making it easy to imagine rowdy nights here in the 16th century. Close your eyes and picture the pirates as you dig into everything from charcuterie boards and tuna carpaccio to hearty short ribs, grilled Chilean sea bass, and squid ink risotto with langoustines."

"At this luxury collection of six historic homes—some from the 16th century—guests can book a bedroom or an entire house, all within blocks of Santo Domingo’s most important attractions. You won’t find out which room or home you’ll be staying in until your arrival, but you’re sure to be pleased. Located in the heart of the Zona Colonial, the casas are exquisite. Two were part of former convents, one was a monastery, and another was once the private home of a famous Dominican fashion designer. Each one features unique decor and its own courtyard, and five of the six have private swimming pools. Upon check-in, you’ll receive a loaner iPhone to communicate with your house butler and the round-the-clock concierge team, who can help arrange excursions like culinary tours in the Old City and visits to one of the Caribbean’s largest organic cocoa producers."

"A UNESCO World Heritage site, this hotel was the home of Hispaniola’s first governor, Nicolás de Ovando, and one of the first colonial structures built at the top of cobbled Calle Las Damas (the first paved street in the Americas). Built in 1502 and connected in 1974 during a reconstruction ordered by then President Joaquín Balaguer, the three stone buildings retain their original coffered ceilings, massive arches, tile floors, and brick and stone walls. In addition to 92 rooms and suites, including a dozen Imperial Club rooms overlooking the Ozama River and Don Diego Harbor (Room 4015 has a particularly stunning view and gorgeous bathroom), you’ll find a lovely reading nook, gourmet restaurant, lobby mojito bar, and tranquil garden, which features herbs and fruit trees used by the hotel kitchen."