Maybe you would be interested in trips offered by St. Barts Yachts in Charleston, SC. They deliver the new Beneteaus made for charter to the BVI and West Indies. It is a volunteer set up. You get there, they provide board upon arrival (which may be on the boat), provisioning for the trip and the return air fare to your specified destination. The web site is www.st-barts.com. I do not know the person who is choosing the people for deliveries right now, but I do know that it is probably not in your best interest to send a picture of you with the "Cuba - 90 miles" buoy from Key West. Those are a dime a dozen. From the content of your post, you would be a decent crewmate on a delivery. And you can log hundreds of sea miles. Just don''t lie on your resume. If it is as it was years ago, you have to be insured by Lloyd''s, and you have to be onboard what gets to be a tiny boat (even the 45 footers) in the middle of nowhere for almost 2 weeks with people you didn''t know 2 days ago. For instance, if you''re a vegetarian, please say so. It certainly doesn''t count against you, but you will be much happier on your voyage. All in all, it tests your skills, sailing and people (and if you are looking to be a delivery or charter captain, this is great experience).
Best of luck in trying to reason with hurricane season. (Boats are delivered 12 months out of 12, so this isn''t just a little jingle.)