The only idea that occurs to me is a crewed charter
. Not my area of expertise but google
"crewed charters" or "captained charters" for Florida
or the Caribbean
and you will find lots of options.
A crewed boat large enough to carry eight passengers would probably start at $10-$15,000/week and go up from there. Florida
to PR is close to 1000 miles upwind so could be a bit of a trip. If you take your time to see the sights could easily take a month. I did in in two months and could have taken longer but had to get back to work.