Volunteering as crew on a passage
is an excellent way of gaining experience. Provided you choose who you go with wisely, you get the benefit of their experience. You'll learn a tremendous amount, much faster than just heading out on your own.
The Chesapeake would be a good place to start with a charter
, if only because there are lots of destinations and it's not full-on ocean, even though in bad weather
it can be just as nasty, or worse. But the anchorages
are sheltered and it's easy to day hop from one place to another. TowBoat U.S. is always a call away and the CG is all over the place.
would be good but you're layering on top a bunch of other concerns that are bureaucratic and logistical. Also, it would be more expensive. North Carolina
has some great cruising grounds in Albermarle and Pamlico sounds. SC, not so much as it's mostly ICW
and a few bays here and there. Not sure what the charter situation is up on Long Island Sound
but that would be another excellent place to start out.