The Caribbean island chain begins 50 miles from the United States coast, but the nearness of an island does not always make it easy to reach. The total travel time and the frequency of flights make some islands more difficult than others to get to from U.S. gateways. Islands like the Bahamas, Jamaica and Puerto Rico have more flight options, making them easier to reach than some others in the Caribbean.


The 700 islands and cays in the Bahamas are less than an hour away from Miami by air. Bimini is the closest island to the U.S. coast, just 50 miles east of Miami. Three major U.S. carriers have flights daily from New York, Atlanta, Charlotte, N.C., or Miami. Two other U.S. airlines have daily or weekly service. Bahamas Air also has seven nonstop flights daily from Miami and two from Fort Lauderdale, Fla.

Many visitors choose Nassau, the island with the most direct flights from major U.S. cities. Cruise ships often dock at Freeport, Nassau or Paradise Island. The Bahamas Tourist Office claims that the water is so clear that you can see underwater delights at depths of as much as 200 feet. The weather is sunny all year, even during most of the hurricane season – June through October. American citizens do not need visas to travel to the Bahamas, but they will need valid passports to re-enter the United States.


Six major U.S. airlines and one low-cost carrier offer daily flights to Jamaica. Air Jamaica also serves routes from Baltimore, Chicago, Fort Lauderdale, New York, Orlando and Philadelphia. The Jamaica Tourist Board notes that most tourists enter Jamaica at Sangster International Airport in Montego Bay. This entry point puts you in the best position to reach resorts and beaches at Negril, Montego Bay and Ocho Rios. The flight from Miami takes 90 minutes. From New York and other cities in the Northeast, your flight will take just over three hours. Norman Manley Airport is a good alternative if you want to visit the capital city of Kingston, Port Antonio or the coffee plantations in the Blue Mountains. Frommer's notes that visitors can find discounted Jamaica travel packages offered by airlines, travel companies and last-minute booking websites. Bring your passport.

Puerto Rico

Puerto Rico is a Caribbean island with a twist; it is part of the United States. The culture is decidedly more Hispanic than American, but you won't have to change currency when you arrive. The island also serves as a connection point for regional Caribbean airlines, making it easy to book side trips to nearby Aruba or the U.S. Virgin Islands. The trip from Miami is just over three hours. Six major U.S. airlines serve Luis Munoz Marin International Airport in San Juan, according to Fodor’s. You won't need a passport to travel to or return from Puerto Rico, nor do you pay duty on items that you bring home. "Travel and Leisure" magazine notes that you can save money on sightseeing by using San Juan's free hop-on-hop-off trolley.