Yachting the Bahamas

If you associate Puerto Rico's capital with the colonial streets of Old San Juan, then you know only part of the picture. San Juan is a major metropolis, radiating out from the bay on the Atlantic Ocean that was discovered by Juan Ponce de León. More than a third of the island's nearly 4 million citizens proudly call themselves sanjuaneros. The city may be rooted in the past, but it has its eye on the future. Locals go about their business surrounded by colonial architecture and towering modern structures.By 1508 the explorer Juan Ponce de León had established a colony in an area now known as Caparra, southeast of present-day San Juan. He later moved the settlement north to a more hospitable peninsular location. In 1521, after he became the first colonial governor, Ponce de León switched the name of the island—which was then called San Juan Bautista in honor of St. John the Baptist—with that of the settlement of Puerto Rico ("rich port").Defended by the imposing Castillo San Felipe del Morro (El Morro) and Castillo San Cristóbal, Puerto Rico's administrative and population center remained firmly in Spain's hands until 1898, when it came under U.S. control after the Spanish-American War. Centuries of Spanish rule left an indelible imprint on the city, particularly in the walled area now known as Old San Juan. The area is filled with cobblestone streets and brightly painted, colonial-era structures, and its fortifications have been designated a UNESCO World Heritage Site.Old San Juan is a monument to the past, but most of the rest of the city is planted firmly in the 21st century and draws migrants island-wide and from farther afield to jobs in its businesses and industries. The city captivates residents and visitors alike with its vibrant lifestyle as well as its balmy beaches, pulsing nightclubs, globe-spanning restaurants, and world-class museums. Once you set foot in this city, you may never want to leave.

Samaná (pronounced sah-mah-NAH) is a dramatically beautiful peninsula, like an island unto itself, of coconut trees stretching into the sea. It's something of a microcosm of the Dominican Republic: here you'll see poverty and fancy resorts, brand-new highways as well as bad roads, verdant mountainsides, tropical forests, tiny villages lined with street-side fruit vendors, secluded beaches, and the radiant warmth of the Dominican people. Samaná is the name of both the peninsula and its biggest town, as well as the bay to the south. It's worth noting that to locals, Samaná denotes only the largest town, Santa Bárbara de Samaná, which makes a great departure point for whale-watching or an excursion to Los Haitises Park across the bay. The bay is home to some of the world's best whale-watching from mid-January to late March. It is now the site of Puerto Bahia Marina and Residences and the Bannister Hotel, contemporary, luxurious yet moderately priced. This complex has brought an entirely new level of tourism to this area, and given yachts a full-service facility in what has always been a desirable cruising destination.A visit here is really about two things: exploring the preserved natural wonders and relaxing at a small beachfront hotel. The latter is most readily accomplished in Las Terrenas, the only true tourist center, where you can find picturesque restaurants, accommodations of all types (including the new oceanfront Sublime Samaná and the luxury condo-hotel, Balcones del Atlantico), and great beaches. At Las Terrenas you can enjoy peaceful playas, take advantage of the vibrant nightlife, and make all your plans for expeditions on the peninsula. The other pleasures are solitary—quiet beaches, the massive national park Los Haitises, and water sports and hiking. A relatively new toll road connects Santo Domingo to the peninsula; it's about a 2- to 2½-hour drive. Small El Catey International Airport is near Las Terrenas and is now being served by twice-weekly JetBlue flights (Wednesday and Saturday). On the Dominican Republic's Samaná Peninsula, the green mountains teem with coconut trees and dramatic vistas of the ocean. The area is full of hidden beaches reachable only on foot or by sea, protected coves, and undeveloped bays. A visit to Samaná is really about two things: exploring its preserved natural wonders and relaxing on the beach. There are a number of all-inclusive resorts where you can hang your hat, quaint and low-key beachfront hotels, as well as new world-class properties, where you can find complete relaxation and tranquillity.

Just 7 miles (11 km) long and a little more than 1 mile (1½ km) wide, this island, the capital and seat of the Turks and Caicos government, has been a longtime favorite destination for divers eager to explore the 7,000-foot-deep pristine coral walls that drop down only 300 yards out to sea. On shore, the tiny, quiet island is home to white-sand beaches, the National Museum, and a small population of wild horses and donkeys, which leisurely meander past the white-walled courtyards, pretty churches, and bougainvillea-covered colonial inns on their daily commute into town. But things aren't entirely sleepy: a cruise-ship complex at the southern end of the island brings about 600,000 visitors per year. That said, the dock is self-contained and is about 3 miles (5 km) from the tranquil, small hotels of Cockburn Town, Pillory Beach, and the Ridge and far from most of the western-shore dive sites. Pristine beaches with vistas of turquoise waters, small local settlements, historic ruins, and native flora and fauna are among the sights on Grand Turk. Fewer than 4,000 people live on this 7½-square-mile (19-square-km) island, and it's hard to get lost, as there aren't many roads.