Among the best golf destinations in the world, Punta Cana is the very picture of leisure. Several of the courses have been designed by professional golfers, making for the perfect sort of kicked-back challenge that you want on a golfing vacation. The beaches here are simply perfect: calm, warm waters that gently lap at stretches of fine white sand. Thrill yourself with a zip-line adventure, clap along with traditional Dominican music at a cultural performance, or explore the magical lagoons of the Indigenous Eyes Ecological Park.

A city trapped in time, Havana captures the imagination like no other. Faded glamour meets careful colonial-era reconstruction with a backdrop of irresistible color. Walk El Malecón, the walkway bordering the ocean; visit Old Havana and the Catedral de San Cristóbal; and listen for salsa music, open-air bazaars and parties that last all night.

The festive city of San Juan is the perfect place to experience true Puerto Rican culture. Get to know its roots by exploring the vibrant neighborhood of El Viejo San Juan (Old San Juan), which consists mostly of Spanish colonial buildings. Flesh out your self-guided history lesson with a visit to El Castillo San Felipe del Morro, a 16th century citadel that’s a UNESCO World Heritage Site. Then reward yourself with a cooling dip at Luquillo or Carolina Beach, then a tasty tour of the Bacardi rum plant.

Nassau teems with Bahamian and British flavor. The capital city of the Bahamas boasts miles of spectacular beaches and stretches of vivid coral reefs perfect for snorkeling. Shop, dine, and sightsee, particularly along busy Bay Street, or if you're a James Bond fan, visit the British Colonial Hotel, which was used as a filming location for two of the Sean Connery-era movies. Visit during the famed Junkanoo Festival to experience a high-energy parade of spectacularly costumed dancers.

The resort town of Negril has some of the most beautiful coastline in the world. Seven Mile Beach is an inviting stretch of golden sand, perfect for sunbathing or taking a dip in the warm Caribbean Sea. Jump into the Blue Hole Mineral Spring for a rewarding adrenaline rush, then take in a kaleidoscopic sunset from the comfort of a beachfront bar.

You're on island time the moment you set foot in Jamaica. Ocho Rios, a port of call for many cruise lines, also boasts some of the most luxe resorts and spas in the Caribbean. And once you've had your stresses melted away in the island sun, you can head out for a night of dancing and reggae music.

The powdery sands of Varadero are as seductive as the soft lapping of the Kawama Channel waves. Famed gangster Al Capone used to frequent the shoreline resorts, and the city still maintains that glamorous luster that’s been historically appealing to high rollers. Mansions-turned-museums are favorite destinations for curious Cuban history buffs. Nature lovers can embark upon a day of adventure, exploring the area’s caves, keys, and virgin forests.

Boutiques, upscale chain stores and street vendors, as wells as casinos and a wide range of restaurants, dance clubs and bars, make Oranjestad a popular destination in Aruba. In addition to shopping, dining and entertainment, the island's capital city offers museums, a butterfly farm, art galleries, golf, historical sites and a marina. The island's colonization by the Netherlands shows in Oranjestad's Dutch colonial architecture, while the buildings' bright colors are distinctly Caribbean.

Situated on Grand Cayman’s west shore, Seven Mile Beach actually now measures only 5.5 miles. But its gorgeous clear waters and coral sands still lure visitors from around the world. Beach bars, such as the Royal Palms, provide drinks and a lively atmosphere, and restaurants abound. Swim with friendly stingrays at Stingray City, shop Seven Mile Shops, snorkel and scuba in the enticing waters around Cemetery Reef. Visit nearby Cayman capital George Town and the fascinating Cayman Turtle Farm.

In St. John's, the capital city of Antigua, farmers markets, candy- colored architecture and the ruins of sugar plantations vie for attention with a kaleidoscope of coral reefs and sailing adventures. Salute the white baroque towers of St. John's Cathedral that dominate the skyline before joining the flocks of cruise passengers on a Heritage Quay shopping excursion. To experience the island's early cultures, visit the Museum of Antigua and Barbuda, housed in a 1750s colonial courthouse.