The Caribbean islands form an arc from Cuba in the northwest -- less than 200 miles south of Miami -- to Trinidad in the southeast, 10 miles north of Venezuela. The four largest islands, along with Cayman Brac -- all part of the Greater Antilles -- are also the closest Caribbean islands to New York City. These islands offer a wealth of beaches, landscapes, food and other diversions to suit the taste of every traveler.


Cuba is the closest Caribbean island to New York City, with its capital, Havana, 1,300 miles from the Big Apple. U.S. citizens must currently have a U.S. Treasury Department license to travel directly to the island. In addition to ivory-sand beaches and turquoise water, Cuba offers visitors colonial architecture, lush landscapes and a look at the results of Fidel Castro's reign, including streets filled with 1950s' American cars. Be sure to stroll Havana's Malecon, or beachfront promenade, and take a steam train through the Valle de los Ingenios, formerly home to 60 sugar mills.

Cayman Brac

Cayman Brac, the second-largest of the three Cayman Islands, is just under 1,500 miles from New York City. Twelve miles long and two miles wide, the island is dominated by a limestone bluff that is a haven for spelunkers. More than 150 caves wind through the bluff, which rises 140 feet above sea level. Brac is also popular with scuba divers, anglers and hikers. The island has fewer than 2,000 inhabitants, who keep their wooden seaside cottages abloom with orchids, bougainvillea and other tropical plants. Don't miss the Parrot Reserve, home to the endangered Cayman Brac parrot.


The capital of the Dominican Republic, Santo Domingo is 1,555 miles from New York City, making Hispaniola -- which the Dominican Republic shares with Haiti -- the third-closest Caribbean island to New York City. The Dominican Republic offers travelers palm-lined beaches, 500 years of Spanish colonial history and local culture in the form of spicy food and merengue music. Don't miss the 12-square-block colonial district in Santo Domingo. Haiti is less developed for tourism than the Dominican Republic, but the country also offers tropical scenery, fine beaches and colonial architecture. Be sure to visit the town of Cap-Haitien on the country's north coast, which has a colonial cathedral, a ruined palace and the largest fortress in the Caribbean.


Jamaica is the fourth-closest Caribbean island to New York City, with Montego Bay at 1,556 miles from John F. Kennedy Airport. The island's scenery includes white-sand beaches, mountains covered in rain forest, caves, whitewater rivers and waterfalls. Take time to appreciate the colonial architecture in Montego Bay, including Rose Hall Great House (, which will transport you to the lives of 18th century plantation owners. Negril's Seven Mile Beach is one of the island's most impressive stretches of sand.

Puerto Rico

San Juan is 1,600 miles from New York City, making Puerto Rico the fifth-closest Caribbean island to New York City. Puerto Rico has unique natural scenery, world-class museums, a vibrant food scene and 4 million residents who are always ready to have fun. Be sure to visit El Yunque, the only tropical national park in the United States. You'll also want to browse the elegant boutiques that line golden-sand Condado Beach. The island's interior is crisscrossed by narrow roads leading to small towns with friendly residents and great bakeries.