By planning well, you can limit your longest
passage to 100 miles or so, so range shouldn't be a problem. Gasoline is readily available throughout the Caribbean (I have no experience in the Bahamas), though on a couple of the less developed islands you will have to transport
fuel in jerry cans from gas stations on shore.
There are also numerous places to
haul out. In the
hurricane season, the risk of storms goes down the further south you get, though it doesn't really get to zero until you get to Trinidad.
How big is your boat? Some passages are pretty challenging, with adverse winds and big waves. I'm thinking about the
passage from the
Virgin Islands to St. Martin. We've done this twice, once departing from St. Croix and the other time from Virgin Gorda. Really unpleasant seas, a total
washing machine. It's the only time my wife has ever been seasick. Of course, we're a sailboat, so this is like a 20-hour passage for us. If you could complete the passage during daylight, it would be less stressful.