Old San Juan, the oldest city under U.S. jurisdiction and second-oldest European settlement in the Americas, blends historic landmarks, pristine beaches, great cuisine, and resilience. Walk cobblestoned streets past Spanish Colonial sites, browse colorful plazas, and visit Castillo San Felipe del Morro, Castillo San Cristobal, and Museo de Arte de Puerto Rico. Then explore El Yunque's rainforest and waterfalls before relaxing on Luquillo Beach.

Spend a glorious day swimming at famed Cane Bay Garden Beach, hiking the island's rainforest and enjoying a scenic drive around this lush island. Swim with dolphins, go sea kayaking or head over to Virgin Gorda and climb down to the famous Baths for a day of swimming and exploring this natural phenomenon. Take home charming local crafts, straw items, artwork and resort wear. Enjoy local fish dishes or perhaps a pub lunch or burger!

With over a quarter of the island set aside as a national park and rainforest still growing, St. Kitts is a stunning tropical escape. Zip through the Valley of the Giants, hike to Sofa Rock atop a still-smoldering volcano, or relax on beaches protected by coral reefs. Enjoy fresh seafood and seasonal fruits like soursop and mammy apples, plus duty-free shopping for copperware, local beer and rum, and embroidered fabrics.

Antigua, especially St. John's, is a classic British Caribbean destination, with 365 beaches, coral reefs, forts, and colonial architecture. See St. John's Cathedral, rebuilt on the same spot three times after earthquakes, and the Museum of Antigua & Barbuda, with island history and semiprecious stones. For nature, visit Nelson's Dockyard National Park or the Shirley Heights trail. St. John's also has nightlife and live music, and local restaurants serve buttery "flying fish."

One of the Caribbean's true gems, St. Barts is where Riviera chic meets Caribbean cool. Day-trippers come from nearby islands for the duty-free shopping, excellent dining and to lounge on the soft, white sands in a secluded palm-fringed cove. Tour Fort Gustav and Fort Carl, historic reminders of Sweden's short-lived Caribbean possession. Excursions abound, inviting guests to snorkel, sail over the clear blue waters on a catamaran, or horseback ride through shaded jungle trails.

St. Maarten is the smallest piece of land shared by two sovereign states. Legend has it that the Dutch and French boundaries of the island were determined by two men who challenged one another in a race around the island, with the Frenchman walking faster and claiming more land. Legend or not, both the Dutch and French settled here in the 1630s and despite occupancy by the British twice, the Dutch and French have lived peacefully together ever since they arrived.

Discover tax-free shopping heaven in Charlotte Amalie, the Caribbean's Mecca. Beyond world-class beaches and snorkeling at Coki, Sapphire, and Trunk Bay, the shopping is unmatched: designer shops on Main Street and countless stores in the side streets. Find jewelry, watches, china, liquor, linens, tobacco, and rum balls. Pause for a creative rum cocktail, then head to Frenchtown for a great meal in lush tropical surroundings.

Discover La Romana, a luxurious resort town with sugar-white beaches and pristine turquoise waters. Visit Altos de Chavón, a beautifully recreated Mediterranean village perched above the city, with cobblestone streets, the Church of St. Stanislaus, and the Regional Museum of Archaeology. Browse La Marina's boutiques and galleries for Larimar and amber jewelry, designer clothing, fine hand-rolled cigars, embroidered linens, pottery, fine art, and woven crafts.

The 700 islands of the Bahamas Islands begin 50 miles off the coast of Florida, stretching 760 miles to the southeast. The heritage of Old Nassau blends the Southern charm of British loyalists from the Carolinas, the African tribal traditions of freed slaves, and a bawdy history of blockade-running during the Civil War and rum-running in the Roaring 1920s. Over it all is a subtle layer of civility and sophistication, derived from three centuries of British rule.

Sunny Florida skies, year-round warmth, nightlife, and a diverse culture define this cosmopolitan city. South Beach draws crowds, while the Art Deco District is the world's largest collection of Art Deco architecture. Shop from Bal Harbour to Lincoln Road and Coconut Grove, enjoy Cuban culture on Calle Ocho, or visit the historic Venetian Pool. There's something for everyone in this "Gateway to the Americas."