Well, I just had this random idea the other day how it would be really cool to be able to crew a sailboat and sail somewhere. In my logic it would be neat because I’d get paid and be able to do something that I’ve always dreamed about. Have any of you dopers out there known, or actually done this yourself? Is it hard to do and was it worth it in the end? I am totally clueless about any of this, so please be gentle 
From people I know who sail in Australia the opportunities are mostly in racing or returning boats after races. There are links here that may be of interest.
My nephew worked on a tall ship at age 17. However, he was an experienced sailor – he sailed Sunfish from about the age of 5, and was used to sailing on my father’s sloop.
The first question is how much experience do you have? If you’re want to be hired as a sailor, you need to know your way around boats. If someone told you to slack off on the main sheet, would you know what to do?
If you have experience sailing, then you probably should hang around the harbor, make yourself useful, make friends, and hope that something might happen.
Well, my first assumption is that you mean a smaller (20-60ft) private sailboat. My comments don’t apply if you mean something bigger and more akin to a cruise ship with paying customers.
If you have a lot of experience captaining a vessel, you can get gigs delivering boats or perhaps ‘assisting’ a inexperienced owner on a difficult passage. However, as a fairly novice crew memeber, you will most likely have to work for free (most people have no problems with this and simply wish to get experience at sea). In fact, some boats will expect you to pay a share of your food while on board.
If your object is to simply spend time on a boat, as opposed to traveling to faraway place, try going down to the local yacht club and seeing if any of the racing yachts need additional crew members. Most boats are always happy to have another crew member, if only to add ballast “on the rail” (basically sitting on your butt as close to edge of the boat as possible, to prevent excessive heeling).
A friend of mine volunteers on theAlexander von Humboldt , a German tall ship. Everyone on board helps to sail, but most of each crew are newbies, so each trip is a training trip. Trainees have to pay to sail. There is a core crew (unpaid) of experienced sailors. It would probably help if you speak German.
After college, one of my friends did a SEA semester , a similar program out of Woods Hole, MA.