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.