In 1989/90 I sailed across the Pacific Ocean from Los Angeles to Sydney. Hitching on sailboats is easier than it sounds. I took 10 different boats, mostly on the west coast of the Americas.
Ten different captains and ten slightly different agreements for passage. Mostly, it was berth space, food and passage in exchange for some work around the boat and especially steering and adjusting sales.
In one case a skipper asked me to pay 1/4 of the diesel fuel bill for the passage, so I would sail as much as possible. We sailed a lot, even with very little wind and when we arrived in Panama he declined my offer to pay my agreed share, saying he just wanted to cut fuel expenses which we did.
Most sailboats are owned by persons of affluent background and they want to sail with their friends. Often their friends think it is a good idea and agree to come along and then find out that sailing is not their cup of tea (too dirty, bumpy, boring, cramped - any number of reasons). Thus crews are constantly unexpectedly reforming. This is your opportunity for a ride.
In all the ports I visited in Central America and the South Pacific including Australia at 8 AM local time all the boats in the harbor talk with each other over radio on channel 19. They talk about all kinds of things they need, like where to get the bottoms of boats scraped and where is a good place to buy diesel fuel that is not watered down. At the end of this broadcast I gave my name and said: "I am looking for a ride to the Marquesas and I can navigate."
The four capabilities that boat captains are most often looking for are
I mostly choose navigation, since I am good with math and dangerous with cooking. Learning navigation is relatively accessible, by going to a course or getting a book.
The navigator also turns out to be one of the easiest jobs, because almost all sailboats going long distance have satellite navigation systems which make directing the boat relatively easy. Navigators, like medical folks, are to be able to deal with emergencies, specifically lightning hitting the boat.
The author Paxus Calta-Star is organizing a tree house sustainability wind festival in the Ozarks called Villages in the Sky. June 1 thru 6 2010. Build up camp is happening right now; come volunteer to build zip lines, micro wind turbines and giant play structures in the trees.