If you manage to catch a ride on an outbound boat, don’t worry about the destination (other than t’have documentation appropriate for foreign ports, if applicable). Sailboats are almost always coming from or going to other places with sailboats, where further opportunities will present themselves. If you have a bad experience, move on; don’t bad-mouth skippers or boats; it’s a smaller community than you’d think, and it might come backatacha.
If y’feel unsafe aboard a particular boat, or see something aboard that causes you concern, go ahead and ask, but be prepared to get an unsatisfactory answer. Many times, in trying conditions, green hands have compromised ship’s safety through their fear. The captain aboard a ship at sea is next to God, so you had best resign yerself to following their lead. Rarely, one will encounter a skipper who is pleasant enough in port, but turns into a drunken bullying tyrant at sea, but these are exceptions to th’rule.
This leads me t’discuss the hardships of sea service. Often i tell folks about the beauty and rewards of the sea, or of the (sometimes) great pay. Yes, it is possible to make $200+/day sailing in tropical paradise, but y’must be prepared for some hardship t’get there. I once worked 72 16-hour days in a 3-month period. I later worked 82 8-hour days in a 3-month period. Both were aboard traditional sail-training vessels; the former was for pay, the latter as a volunteer. Still, this is nothing compared to some commercial crew aboard working merchant vessels, who might work 12-16 hour days for 6 months on end.
Then, there’s the living conditions. Especially aboard sailboats, you’ll find no privacy, no real personal space, and little room for possessions. However, this can lead to some great crew bonding. Read this here for a great example. You need to be available to serve the ship 24/7, whether standing a watch or being ready to leap out of yer berth and go aloft to clear some foul at night in miserable weather.
The upshot is that you have to be prepared for some personal sacrifice and hard hard work to get the most out of what sailing has to offer. But, when all is said and done, it’s rewarding beyond anything else in my experience.

While yer doin’ yer readin’, start thinking about what sorts of boats you’d like to ship on. For a lubber, by far the best experience will come aboard a tallship, but there’s other routes. If yer near water, find a local yacht club and ask when they hold their race days through the local sailing season (there’s a summer wednesday night series in Vancouver), and see if you can get yer name on a crew list. Failing that, just show up ready to work on a race day, and start asking at every boat that looks to be heading out. If you’re truly green, don’t worry; many skippers are happy to have an extra eager and obediant hand sit on the rail (railmeat) or grind th’genny winches. Even if yer overwhelmed, just be quick and don’t ask too many questions. A nice afternoon race on a well-founded 30′-40′ boat will expose you to every possible combination tacks, jibes, sets, and take-downs than you’ll likely see in weeks of casual cruising.
On modern boats, delivery/voyaging crew are always in demand, but be wary of the “pay to crew”, which can run you $50-$200/day. “Cost sharing” is another popular way to crew, where you pay for your own food and a portion of operational expenses. Some owners set the cost-sharing amount, while others budget on the fly. If a skipper can’t give you an upfront estimate of shared costs, be skeptical; an experienced voyaging captain can tell you their daily shared crew expenses from previous voyages. Remember, y’can always spend more money than estimated, but seldom any less, so watch that bottom line. My favourite place to start looking for these jobs is This Site. The really good ones are few, but the postings there will give you a good idea of when/where the delivery work is, season to season. If you see alot of work in one area (for instance, Eastern USA to Caribbean in November), and can get to those areas, go take a look in person. Look fer ads in marinas, or boats that look ready for offshore (steering vanes, liferafts, spares lashed down everywhere, etc.) and approach the owner. The foremost qualification for delivery/voyaging crew is character, not ability. You can learn most of the skills you’ll need, but if you can’t live in a tiny space together with th’rest o’th’crew, yer sunk. Skippers will want t’know if they can get along with you before they want t’know what you’ve read or where you’ve been.
For tallships, the ASTA website is a good place to start; check the “Billet Bank”. Apply, or better yet, just show up on the dock with yer seabag packed. This is known as a “pier-head jump”, and is really the best way to get aboard. Schooners and tallships, whether daysailing harbour-cruisers or offshore sailtraining vessels tend to have notoriously fluid crewing arrangements; if they don’t need crew today, wait ’till tomorrow. If they don’t need sailin’ crew, volunteer dockside; traditional boats are undergoing endless maintenence, and extra hands for this labour are always appreciated. You’ll get to know the crew, and might just catch a berth after all. If nothing presents itself, be persistant!