The Caribbean might sound like one homogenous collection of islands to many tourists, but anyone who’s been to its disparate countries and territories knows that numerous cultures, cuisines, landscapes, and experiences can be found among its crystal-clear waters. The region is comprised of 28 independent countries and dependent territories. A notorious pirate haunt for centuries, the Caribbean was the Wild West of the Old World for centuries, and was long coveted by its monarchs. To this day, the English, French, and Dutch have footholds here. The Spanish would have as well, were it not for the U.S., but their 300-year rule in these lands can still be felt in Puerto Rico, Cuba, Dominican Republic, and Mexico.
It’s almost impossible to describe the Caribbean as a whole (unless “sunny with plenty of beaches” counts as a description!). And for many travelers, it’s equally difficult to choose one Caribbean destination. Do you want the colonial charms of Old San Juan in Puerto Rico or the pink-sand beaches of the Bahamas? Do you prefer the picturesque waterfalls of Jamaica or the shipwrecks off Cayman Islands?