You can do anything you want - people row across the Atlantic. Some sail across in what we would call a dinghy. Would I do it? No, but I'm not going to stop you. The problem most here are pointing out is that the shallow draft, coastal cruiser that you want in the islands makes sense. But it is a different boat than one purpose built for some of the big water passages you will make to get there. One thing you might consider is buying the 320DA and having it shipped to your island destination. When you figure the costs, time, wear and tear, danger, etc., you might find it an attractive option. My other advice would be to go spend a month in DR and spend that time talking to locals about what is reasonable there. Save the boat shopping for step 2.