Z Axis "I'm Sailing!"

Life is full of dilemmas. Obviously one of the big ones for me is to take a serious job or to keep on bumming around planet earth for the foreseeable future? And if I do take option "B", how the hell do I keep it up. I can't buy an RV, i couldn't afford it and even if I could I'd have to run it on biodiesel to not feel guilty about it. I can't go take out a mortgage on a house, because that pretty much kills your travel ability ( oh yeah, and I'm broke at the moment as well).
To get to the point, it occured to me not to long ago that the ultimate mobile lifestyle, and one that would allow me to chase that "endless summer" would be to live on a boat. More specifically a sailboat (the whole fuel cost/greenhouse gas emissions of running a motor all day wouldn't really sit well on the conscience).
Also, because I'm an addicted rock climber, it seems at first blush that being in the ocean makes it slightly more difficult to access a lot of rocks, (that is unless I were to pioneer the sport of underwater rock climbing. Given the fact that the largest mountain ranges are underwater I could put up more first ascents than anyone in history. Of course i could also alter my gravity settings with my SCUBA gear, but given the fact that I'd be climbing in flippers I'd say it would just about even out in terms of difficulty....) ANYwhoo after some serious thought I've given up on the idea of underwater climbing because I realized that there is a wealth of good rock near the ocean. Here's a list of places i've thought of.
-Southeast Asia (Tonsai/Railay and all of the Thai Islands like Phi Phi, Lao Liang and Ya Noi), also in SE Asia, Malaysia, Taiwan and the Philippines.
-Squamish, BC- You can sail right into Howe Sound and be at the crags in a short bike ride (the boat should have bikes) Tons of granite crack climbing at my fingertips.
-The Mediterranean- Between Spain, France, Mallorca, Turkey, Croatia and whatever other amazing places i've just left out, there is a lifetime of boat accessible climbing here.
-Maine Acadia National Park
-California- The lost coast
-New Zealand- Golden Bay.
-All of the other awesome places that I couldn't think of

Another Dilemma: I have no idea how to sail and I don't own a boat.
Solution: It turns out that you don't have to own a boat to get on a boat sailing around the world.
Back in 2003 I stayed with this couple in New Zealand. The guy was from England but had gotten to NZ, where he now lived via a boat that he hopped on in the Panama canal. Yachty types apprently flock from the pacific to the Carribean like clockwork every year, a lot of them going through the Panama Canal and looking for a few extra crew members. Anyhow there is vast opportunity to hop on boats that way.
I did some research recently and there are website devoted to hooking up potential crew members with captains looking for crew. Below are some of the links. (one of the links is for a boat where as crew you promise to teach english at the many stops along the way.
-floatplan.com
-the peace boat

Needless to say I've got a posting on floatplan already promising to trade climbing lessons for sailing lessons. Lets see if I can't get all Bill Murray-ish like in What About Bob, I'll keep you posted.