Re: Do it all boat, Caribbean and Rtw
I agree with PB's comments. You need to provide more information. Budget is an obvious one. Also there are RTW trips and other RTW trips. Some require much more boat than others because the conditions can be much worse. If budget allows, a fundamental question is mono versus cat. If we could afford it $250k or more, my wife would love a good catamaran - me, not so sure. I am currently at an anchorage in Indonesia with about 40 boats nearby. The only brands with more than one example are Amel (3), Halberg-Rassy (3), and Beneteau (2). The first two brands are quite expensive. The Beneteaus you see are usually quite large - the 50s are common or are in the Oceanis line. There is one large Island Packet in the rally but you don't see them that often when you get a long way from North America.
I think you are placing way too much concern on shoal draft (our Bristol is a centerboard with 5' draft and it was only useful in the Bahamas. Not a help elsewhere. If I was buying, IP would be far down my list.
Heading back to Lake Ontario for this summer. Relatively few stops along the way from Grenada. Martinique, Guadeloupe, St. Martin (must have something to do with the French food), then Bermuda, New England and up the Hudson/Erie Canal. We were going to go via Newfoundland and Labrador but June remembered that one of the kids is getting married this summer - details, details!