Save the money and deliver sailboats. Large market for trained crew to take yachts from Point A to Point B. :) No people except those you bring. Free yacht.
If you want to drive the boat yourself and not get too many questions, you probably want to start looking at a Captain's license. That requires a number of hours on the water and a test. The same is typically required or at least desirable if you want to run a chartering business.
https://www.uscg.mil/nmc/credentials/charter_boat_capt/
RE experience, if you're totally new to sailing I'd start first with some basic sailing expertise at a sailing academy. J-World and others offer "learn to sail" courses as well as cruising courses. An American Sailing Association boat-handling certificate is probably useful as "proof of experience" for future crews. US Sailing's "Safety at Sea" typically run annually in different cities is another good one, and required for most off-shore regattas.
Once you've got the basics down, I'd suggest being a ride-along with a more experienced skipper / crew. Places like Offshore Passage Opportunities provide listings of folks looking for crew, but I'd recommend due diligence if you decide to make the passage:
https://www.sailopo.com/
You might also get yourself on a mailing list for local regattas or sailing forums and say you're looking to help with deliveries. How long / where these things happen will likely vary by region. People do transits from Florida to Carribean all the time. Same with New England to the South each year. Racing boats go from Mid-Atlantic / New England to Florida / Key West around end of the year. In Midwest, deliveries from Mackinaw are common in July after the Mackinaw races. West Coast - not sure, but Transpac (Hawaii - SF) returns and/or Coastal races are probably common.
You can get started fairly easily. Take a sailing course that gives you a recognized certificate. For example, the RYA "Competent Crew" or "Day skipper". Different countries have different certifications that are recognized worldwide. The UK Royal Yachting Association (RYA) is definitely one of them, and you can do these courses in lots of sail training facilities across Europe.
From there you can jump on almost any boat delivery crew with a bit of luck.
Most rich boat owners don't want to sail their yachts across large bodies of water, so they employ delivery crews. Normally they employ an experienced captain and the captain hires his/her own crew.
Boats are normally moved during the spring months from Europe to the Caribbean, specifically for the start of the season for Antigua Race Week, which I believe takes place in April/May. They normally head out from the Mediterranean via the Canary Islands to cross the Atlantic.
Common places to jump on board are where yachts have been kept or serviced over the winter. Common ports include places like Palma de Mallorca, which is full of "boaties" looking to get a place on a yacht crossing. You hang out in the "boaty bars" and see if you can hook yourself a ride by chatting to people. There are also a number of internet forums, but you'll get better luck face to face, and you'll spend a number of weeks with these people in close confinement, so you'll want to know what they are like beforehand.
As you get more experienced and depending on the boat you could try to get taken on permanently by the owner. The pay on the super yachts of the super rich can be insanely high, especially for experienced captains, chefs and engineers - monthly 5 figures if you are really good. That being said the super rich can be complete assholes, who can start throwing the carefully presented lobster dish back in your face because it wasn't the right colour, or you forgot to make sure the wine fridge was stocked with enough Dom Perignon P3 Plenitude Brut.
I've heard some wonderful stories of the super rich from boaties. It's a crazy life.
Just a heads up that a friend of mine worked in this direction for years but was rejected from a captain's license because he had that partial color-blindness thing lots of people have, and that reportedly was enough to disqualify him permanently. Most of a decade "wasted" (if wasted is defined as sailing yachts around the Med and picking up languages). He now sells wines in Sydney, with the benefit of correct pronunciation in four or five languages.
That's really interesting - makes sense, however as the main nautical colors are red and green. Messing them up would mean the difference between avoiding a ship and hitting it. Never thought about how bad a color choice that was for lights!
