Tortola, Charleston, Newport & More

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.

From the bioluminescent bay of Fajardo to the vibrant art scene in Santurce, every part of the island of Puerto Rico glows. Punctuated by El Yunque rain forest and crisp, white beaches like Condado and Isla Verde, San Juan is perfectly located to easily access all its geographical diversity.

Nestled in the sea of tiny islands that make up the British Virgin Islands, Tortola, the archipelago’s largest and capital island, stands out for all the right reasons. An idyllic blend of ancient ruins, iridescent lagoons, lush mountains and white-sand beaches, this Caribbean utopia is perfect for sailors from all walks of life.

San Felipe de Puerto Plata is the capital of the Puerto Plata province on the Dominican Republic’s Atlantic north coast. The city is best known for its beaches. Playa Dorada’s lengthy beachfront is backed by resorts and an 18-hole golf course. The city’s old colonial-era center is dominated by the 16th-century Fortaleza San Felipe, a Spanish fortress that now houses historical and military artifacts.

Tucked between the Cordillera Mountains and Atlantic coast, Puerto Plata embodies geographical duality at its best. A day here can include vegging out on the snow white beaches of Playa Dorado, or hiking through the jungle to the 27 waterfalls of Damajagua and careening down via natural slides. Or you can jump right in. We won't tell you how to live.

Wandering through the city's famous Historic District, you would swear it is a movie set. Dozens of church steeples punctuate the low skyline, and horse-drawn carriages pass centuries-old mansions and town houses, their stately salons offering a crystal-laden and parquet-floored version of Southern comfort. Outside, magnolia-filled gardens overflow with carefully tended heirloom plants. At first glance, the city may resemble a 19th-century etching come to life—but look closer and you'll see that block after block of old structures have been restored. Happily, after three centuries of wars, epidemics, fires, and hurricanes, Charleston has prevailed and is now one of the South's best-preserved cities.Although it’s home to Fort Sumter, where the bloodiest war in the nation's history began, Charleston is also famed for its elegant houses. These handsome mansions are showcases for the "Charleston style," a distinctive look that is reminiscent of the West Indies, and for good reason. Before coming to the Carolinas in the late 17th century, many early British colonists first settled on Barbados and other Caribbean islands. In that warm and humid climate they built homes with high ceilings and rooms opening onto broad "piazzas" (porches) at each level to catch sea breezes. As a result, to quote the words of the Duc de La Rochefoucauld, who visited in 1796, "One does not boast in Charleston of having the most beautiful house, but the coolest."Preserved through the hard times that followed the Civil War and an array of natural disasters, many of Charleston's earliest public and private buildings still stand. Thanks to a rigorous preservation movement and strict architectural guidelines, the city's new structures blend in with the old. In many cases, recycling is the name of the game—antique handmade bricks literally lay the foundation for new homes. But although locals do dwell—on certain literal levels—in the past, the city is very much a town of today.Take, for instance, the internationally heralded Spoleto Festival USA. For 17 days every spring, arts patrons from around the world come to enjoy international concerts, dance performances, operas, and plays at various venues citywide. Day in and day out, diners can feast at upscale restaurants, shoppers can look for museum-quality paintings and antiques, and lovers of the outdoors can explore Charleston's outlying beaches, parks, and waterways. But as cosmopolitan as the city has become, it's still the South, and just beyond the city limits are farm stands cooking up boiled peanuts, the state's official snack.

Loaded with historic sites, cobblestone streets, horse-drawn carriages and unique architecture, Charleston is one of a kind.

Established in 1639 by a small band of religious dissenters led by William Coddington and Nicholas Easton, the city by the sea became a haven for those who believed in religious freedom. Newport’s deepwater harbor at the mouth of Narragansett Bay ensured its success as a leading Colonial port, and a building boom produced hundreds of houses and many landmarks that still survive today. These include the Wanton-Lyman-Hazard House and the White Horse Tavern, both built during the 17th century, plus Trinity Church, Touro Synagogue, the Colony House, and the Redwood Library, all built in the 18th century.British troops occupied Newport from 1776–1779, causing half the city’s population to flee and ending a golden age of prosperity. The economic downturn that followed may not have been so great for its citizens but it certainly was for preserving Newport’s architectural heritage, as few had the capital to raze buildings and replace them with bigger and better ones. By the mid-19th century the city had gained a reputation as the summer playground for the very wealthy, who built enormous mansions overlooking the Atlantic. These so-called "summer cottages," occupied for only six to eight weeks a year by the Vanderbilts, Berwinds, Astors, and Belmonts, helped establish the best young American architects. The presence of these wealthy families also brought the New York Yacht Club, which made Newport the venue for the America’s Cup races beginning in 1930 until the 1983 loss to the Australians.The Gilded Age mansions of Bellevue Avenue are what many people associate most with Newport. These late-19th-century homes are almost obscenely grand, laden with ornate rococo detail and designed with a determined one-upmanship.Pedestrian-friendly Newport has so much else to offer in a relatively small geographical area— beaches, seafood restaurants, galleries, shopping, and cultural life. Summer can be crowded, but fall and spring are increasingly popular times of the year to visit.

Newport has all the quaint charm of a rustic New England with the luxury and conveniences of any nearby city.

From Wall Street's skyscrapers to the neon of Times Square to Central Park's leafy paths, New York City pulses with an irrepressible energy. History meets hipness in this global center of entertainment, fashion, media, and finance. World-class museums like MoMA and unforgettable icons like the Statue of Liberty beckon, but discovering the subtler strains of New York's vast ambition is equally rewarding: ethnic enclaves and shops, historic streets of dignified brownstones, and trendy bars and eateries all add to the urban buzz.

Always on the cutting edge of culture, New York City’s constant reinvention of itself makes it a can’t miss hub of art, theater, food, and fun.