>>1118891ive posted about sailing a few times on out.
its not as expensive as you might think, i bought my 18 ft. buc for $800 and dry dock fees at the marina are $350 a year. (pic related)
there are schools but ive never taken classes. i might someday just for shits and grins.
ive never sailed under a captain of a yacht or been a part of a crew but know many sailors who have.. all of them got their gigs by working at yacht clubs or marinas.
if your by yourself start small with a laser or a tasar. something you can sail yourself or with one other person.