Learn to sail!!
I sailed in a large group of boats from the Canaries to the Caribbean a few years ago. Its an event called The ARC. We then sailed on our own through the islands over a period of 4 weeks. It was a fantastic trip and not expensive because (a) we had our own accommodation (b) we ate on board a lot and (c) it was not my boat so I did not have to pay all the acquisition and maintenance costs. We split all running costs.
I did not get an impression of it being backpacking territory ( Guadaloupe, Dominica, Antigua, Martinique) more Cruise Ship territory where US tourists drop off, are whizzed around in air con coaches and then return to luxury ships. We were in marinas though and I formed a very strong impression of being barricaded from the real islands. I loved the weather but would be reluctant to return to that area because of the feeling/perception of being kept apart. I specifically hated Antigua apart from the wonderful buildings and facilities in Nelsons Dockyard and English Harbour. Rich mans paradise and poor mans window shopping at its best.
mf