I've only ever been to Jamaica, so I would have to say there, because it's so laid back and I think the best place for folk such as we.
The BF once did a charter sail to the caribbean - lucky s0d took in Antiga, Grenadines, Virgin Islands, Caymans, St Lucia , Puerto Rica, Dominica and god knows how many others. Why he ever came back I don't know... (he didn't know me then !!)