San Juan, Puerto Rico's capital, blends old and new. Founded in 1521, it was a key Spanish colonial port; El Morro still guards the harbor. Old San Juan, behind thick stone walls, keeps blue cobblestone streets, plazas, and colorful heritage buildings, and serves as the island's cultural hub. Nearby Santurce is the trendiest district, with shops, restaurants, and nightlife. Minutes away, Condado and Isla Verde offer iconic palm-lined Atlantic beaches.

Jost Van Dyke, the smallest of the four main British Virgin Islands, has fewer than 300 residents on just 3 square miles. They warmly welcome sailors and yachtsmen who anchor in Great Harbour and White Bay year-round. Life centers on the sea-swimming, snorkeling, fishing, and diving-and on tropical drinks and fresh seafood at its famous beach bars and restaurants. Rugged trails cross the island; the toughest, for seasoned hikers and 4x4s, climbs Majohnny Hill for panoramic views from 1,000 feet.

St. John, the smallest of the three main U.S. Virgin Islands, is a pioneer in Caribbean eco-tourism. Over half its 20 square miles are undeveloped, protected as Virgin Islands National Park, created in 1956 from land donated by Laurance Rockefeller. Its beaches, coast, and seas are also protected. Days center on hiking, swimming, snorkeling, and sailing. Cruz Bay is the commercial hub and ferry landing from St. Thomas. A winding road leads to quiet Coral Bay and its sheltered harbor.

Grand Turk is known for its gorgeous beaches and impossibly clear, shallow water that shades from pale to deep blue. Step off your yacht onto pearly white sand, then snorkel or dive the offshore reefs or Gibbs Cay, where you can swim with friendly stingrays. The modern cruise center offers duty-free shopping, a large Caribbean pool, and Margaritaville, while Cockburn Town's colonial architecture and the Turks and Caicos National Museum add history.

Once a Prohibition-era haven for rum runners and anglers, Bimini is just two hours from Miami and long known for fishing, gambling, hotels, and nightlife on North Bimini's beaches. Hemingway helped make it famous in the 1930s. Today visitors snorkel and dive at a shipwreck and Bimini Road, and visit nearby reefs like Rainbow Reef and Tuna Alley. Sharks and stingrays are studied and protected at the Shark Lab on South Bimini.

Stroll Miami's world-famous beaches and soak up its electric energy. Explore South Beach's Art Deco District, with 1930s pastel hotels and tropical motifs. In Little Havana, grab a legendary Cuban sandwich and a strong, sweet café Cubano. Or relax on 12 miles of sandy beach and watch the world go by. At night, dance salsa, unwind in a candlelit lounge, or party until sunrise.