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.
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.
Best of luck! :)