learn to sail and pass some crew qualifications then you can
a friend of mine used to crew a 66 foot yacht for a rich banker, yacht was based in Antigua. She used to get paid considerably more than I do (as a civil engineer) tax free, had no accomodation costs and could use the bankers money to buy diving gear and windsurfers etc. for them to play with.
( Vipros. clever got me this far, then tricky got me in, Wed 16 Jun 2010, 15:03, 2 replies, latest was 16 years ago)

I've read about people going around the world and skippering ships here and there
some guy I read about became a boat deliverer based in the Bahamas. *jealouses*
( Kitty v1.0 desperately naive, Wed 16 Jun 2010, 15:04, Reply)

you need to have some connections I guess
my friend used to row competitively (and has family who were big sailors near southampton) and she wangled a position crewing the support boat for the cross atlantic rowing race (the one where fogel and cracknell were naked)

she ended up in Antigua and through contacts got a job on this bankers boat. then the old skipper got fired and she got her boyfriend the skipper job.
( Vipros. clever got me this far, then tricky got me in, Wed 16 Jun 2010, 15:06, Reply)

I think my dad has some connections
albeit of the crew side of things rather than the rich people side. I've heard that it's possible to do it by sailing a lot and getting to know the fellow sailors in ports, or in large canals where they have a pilot, etc.
( Kitty v1.0 desperately naive, Wed 16 Jun 2010, 15:22, Reply)

Then
What are you waiting for?
(Aberracion Life's getting very complicated, but a lot of fun., Wed 16 Jun 2010, 15:24, Reply)

For Wiggy to get excited about it and go "hell yeah let's go"
Also, the sensible side of me suggests I should finish at least one degree in my life!
( Kitty v1.0 desperately naive, Wed 16 Jun 2010, 15:25, Reply)

Again
It sounds like a brilliant plan, but I get sea sick.
(Aberracion Life's getting very complicated, but a lot of fun., Wed 16 Jun 2010, 15:06, Reply)