The islands of the Caribbean Sea or West Indies are an extensive archipelago in the far west of the Atlantic Ocean, mostly strung between North and South America. They've long been known as a resort vacation destination for honeymooners and retirees, but a small movement toward eco-tourism and backpacking has started to open up the Caribbean to more independent travel. With year-round good weather (with the minor exception of hurricane season in the late summer and early fall), promotional air fares from Europe and North America, and hundreds of islands to explore, the Caribbean offers something for almost everyone.
The Caribbean islands were first inhabited by the Arawak Indians, then were invaded by a more aggressive tribe, the Caribs. Unfortunately, the Caribs could not appreciate their victory for long, for the Spanish, Portuguese, Dutch, French, and British, colonised their lands. The islands have known many historic battles - and more than a few pirate stories. Recent archeaological research shows that the story of the aggressive and even cannibalistic Caribs (hence the name) is outdated.
The westernmost islands, to the east and southeast of Florida, are mostly relatively large (hence the name).
Between the Greater Antilles and the north coast of South America are dozens of small tropical islands.
You can find information about the local airlines at Caribbean Airliners .
LIAT Airlines  offers an air pass to travel between most of the islands of the lesser Antilles, for about $500 for one month and is unlimited, but you have to pay each airport taxes.  Air Jamaica  also offers a similar program for about the same price. WikiPedia:Caribbean Dmoz:Caribbean