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North America : Caribbean
The Caribbean islands or West Indies have long been known as a vacation destination for honeymooners and retirees, but a small movement toward eco-tourism and backpacking has started to open up the Caribbean to 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 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.
You can find information about the local airlines at Caribbean Airliners (http://www.caribbeanaviation.com/airlines.htm).
There is an Air Pass (http://www.liatairline.com/island-hopper.htm) to travel between most of the islands of the lesser Antilles delivered by the regional company LIAT Airlines (http://www.liatairline.com/), it costs about 500$ for one month and is unlimited, but you have to pay each airport taxes. Air Jamaica (http://www.airjamaica.com) also proposes a hopping program (http://www.airjamaica.com/carib_hopper.asp) for about the same price.