So basically, if I can get there in 3 days or less, then I can go there?
I hear ya about the 20 knot trade winds. I had my boat out this weekend in the 15-25 knot conditions we had in new York harbor and raritan bay. Even with 2 crew to help stand her up, progress beating into the swells was pretty slow. For a while we could only point almost 90 degrees off the wind, between wind shifts, gusts heeling us to 30 degrees, and the boat just dropping into the troughs killing our forward speed... In the really big drops, I could almost feel the boat shudder a tad... Is that what caribbean trade wind sailing is like? If so, I might just stay in fl ;-)
But just on the numbers, as far as non-storm conditions, what is different between my boat and, say, a cape dory 25? It has almost the same draft, a slightly lower ballast to displacement ratio, and a full keel, just on the numbers and based on the fact that a full keel typically points lower than a fin keel, would such a proven offshore boat do any better beating into a chop in heavy winds? Would any boat under 35' loa do much better?
The full keel will track better and be sea kindlier than your Hunter, plus the Cape Dory has a better build quality that will take the pounding a lot better than the Hunter. I really think that you will only lose a few degrees of pointing ability between the two boats.
Are you asking for informational reasons, or do you have the ability to swap over to a CD 25?
I'd take the CD25 for your Island hopping any day. If you are stuck with the Hunter, then I'd learn to be satisfied with cruising the Florida keys and the Gulf Coast. There's a lot of water to be covered either way, and you won't get bored.
Edit: I see that the Hunter 25 is one of the Cherubini Hunters. Supposedly these are better than later Hunters?