Amid the largest coral reef in the West, this Caribbean island lures anglers, divers, snorkelers, and beachgoers. Fish the flats or head out to blue water to hunt for big game—mahi-mahi, marlin, sailfish, and more. Bring your dive card with you on your cruise to Cozumel and witness all the natural wonders waiting below the surface, like neon tropical fish, swaying sea fans, and vibrant coral colonies. Or, go snorkeling to see the show without a dive card. Curl up on the beach in a hammock with a cold one. At Playa Mia, you can even fly down Twin Twister waterslides.

Go cruise shopping for beautiful Mexican silver, amber, and other artisanal gifts in San Miguel. Or, hop a ferry to charming Playa del Carmen, on the mainland, and stroll along la Quinta Avenida for more inviting restaurants, bars, and shops. Down the coast from Playa, you can explore the ancient Maya city of Tulum, perched impressively on a cliff, overlooking the brilliant sea and powdery beach below. Cozumel cuisine means fresh seafood. Savor the catch of the day served on a banana leaf, or enjoy it marinated in lime juice, cilantro, onion, and tomato. Of course, this is the place for Mexican classics like tacos, guacamole—and margaritas.

No destination blends global finance with the Caribbean lifestyle quite like the Cayman Islands. This upscale destination offers world-class restaurants, designer boutiques, and duty-free shopping, plus white sand beaches, brilliant blue waters, and teeming coral reefs. Enjoy postcard views of George Town, Seven Mile Beach, and West Bay from the custom-designed Cayman Explorer. You can step down easily into shallow waters to interact with the welcoming stingrays.

Launch your snorkeling adventure from a luxurious catamaran. Swim right through the World War II naval vessel USS Kittiwake, now a shallow artificial reef. Finish with leisurely sunbathing and cool cocktails. Swim with the denizens of Stingray City in the crystalline waters of Coral Reef Gardens. After snorkeling with the graceful rays, recharge with an island barbecue on Seven Mile Beach. You'll shop till you drop in the duty-free boutiques of George Town. Find gifts for everyone—including yourself—like china, crystal, jewelry, antiques, and resort wear by renowned designers.

Conch shells were the homes of tasty mollusks. Try Cayman conch in salads, chowders, and fritters. Cruises to Grand Cayman Islands are not complete without a sample of the rich Caribbean curries, and don't miss the fresh produce: coconut, cassava, and plantains. For dessert, have some rum cake.

Encounter Georgian architecture, African culture, cool waterfalls, and blissful beaches around Falmouth, a town forged by flames, rebellions, and pirates. At the redeveloped cruise port, enjoy Jamaican rhythms, local crafts, and duty-free shopping. Cruise to Jamaica and uncover rich colonial history at the 18th-century Good Hope Estate up in the hills, or ride a 30-foot bamboo raft along the lazy Martha Brae River. East of town, discover ancient rock formations at Green Grotto Caves, then continue on to iconic Dunn’s River Falls, where you can climb up the steps as the water rushes all around you. Head west on a scenic drive to Montego Bay, passing the infamous Rose Hall Great House, former home of the White Witch, then taking a swim at Doctor’s Cave Beach. Jamaican cuisine runs mild to wild, a result of British, Spanish, and African traditions. The mild staple of breakfast or lunch is ackee—a fruit with the taste and texture of scrambled eggs—with salt fish. On the wild side is jerk, the legendary flavor of Jamaica—spicy hot, mildly smoky, a little sweet—invented by runaway slaves, now popular around the world, adding a distinctly Jamaican kick to chicken, lamb, pork, fish, even veggies.