You are going to get a lot of different opinions about what is capable and what is not. I know personally of a Beneteau 370 that crossed the pond, with in mast furling to boot. I would rather do it in a boat twice the weight with a full keel. Your island hopper is not the best for taking across the Atlantic, but then again, your pond crosser will not be very comfortable in the islands. IMHO, if you are going to buy a boat for ocean voyages, get one thats already done it and is outfitted for it, why start from scratch, and why take a 200k Beneteau and spend another 100k to outfit it and get it ready?
Great men always have too much sail up. - Christopher Buckley
Vaya con Dios