JRP has good advice, as usual... take lessons, gain experience, learn... What many neophytes fail to realize is that even the BVIs are over 1000nm ESE of Miami - that's a thousand miles upwind in the open ocean... more "over" to the Caribbean than "down" from the ICW.
Getting there is a tougher assignment than island-hopping once you're there.
1984 Fast/Nicholson 345 "FastForward"
".. there is much you could do at sea with common sense.. and very little you could do without it.."
Capt G E Ericson (from "The Cruel Sea" by Nicholas Monsarrat)