When planning a trip to Caribbean destinations looking at flight times and airlines are crucial. New Yorkers and the people of Los Angeles especially should investigate the best airlines and the best place to travel to. Getting a round-trip out of JFK when flying to Mexico can be expensive, but nonstop flights to the clear waters of Barbados may not be so expensive if you know when to go.

The U.S. Virgin Islands have St. Thomas, which is one of the few places Americans can travel without a U.S passport. Bermuda is another close New York travel spot, located only 650 miles off the coast of North Carolina, and is relatively easy to get direct flights to.

Many people think about the Caribbean islands and think of Nassau (the capital of the Bahamas) or Turks & Caicos (Providenciales) for their perfect getaway where they can go snorkeling, scuba diving, or kayaking and overall have a laid-back trip. Finding the right island for you depends on the type of nightlife, water sports, and other activities you are interested in participating in.

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 (next to Grand Cayman), 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 (rosehall.com), 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.

Saint Kitts and Nevis

Only four hours away from NYC, Nevis is a lesser known island that offers a luxury island experience. The island has no shopping malls or cruise lines, the island is reserved for villas and high end hotels. Unlike Nevis, St. Kitts has full itineraries of activities and an active nightlife scene.


Newark Airport is only four hours from Kingston, Jamaica. However, if you fly JetBlue or Caribbean Airlines from New York to Kingston you can be there in about three hours and forty-five minutes.

Other Islands of Note:

  1. St. Martin
  2. St. Lucia
  3. Punta Cana
  4. Grenada
  5. Cancun