Got a friend who is blind and able to get Diamond trained to be a service
animal in exchange for a free cruise
Ridiculous, maybe, but probably easier than the original proposal....
It is legal
for a group to strictly voluntarily share or contribute to the actual expenses of a voyage, but anything beyond that is considered "carriage for hire" and is not legal
for an unlicensed captain
Boat owners with any sense don't want to risk fines, imprisonment (especially Mexican prisons or legal entanglements), or vessel confiscation. Any unlicensed skippers who would take on such a project
may be dangerously ignorant or piratical scofflaws.
And no sane boat owner would want to take on non-sailors who are likely to be sick, miserable, and utterly unlikely to be useful crew, but likely to be in need of significant caregiving from crew.
Also, doing a voyage where passengers don't return on the same vessel or mode of transport definitely adds some bureaucratic/legal complexity.
Captains bear enormous liability and risk in transporting persons not well known to them. Imagine if you will what happens if a passenger becomes injured or ill on a small, slow moving boat that may be many hours or days from medical
attention. Or if a passenger, upon reaching Mexico
, is found to possess illegal drugs or a gun or even so much as one empty shell casing... Bye, bye boat.