Hi, Dan, and welcome to CF!
Is it feasible? You bet, many have done so, before. I suggest you get a copy of Jimmy Cornell's "World Cruising Routes", it will be very valuable for route planning. You will also want to obtain, and learn how to use, pilot charts
. They tell you the historical conditions for the various locations, by month. Here's a link for downloading them: Maritime Safety Information
They are big, so I hope you have a speedy connection. Also, cruising guides
for the areas you want to visit are very helpful. By the way, although it isn't a cruising guide, per se, Liza Copeland's "Comfortable Cruising" http://www.amazon.com/Comfortable-Cr...3900472&sr=1-2
is a great read for much of the area you're thinking about.
Sounds like you're wanting to do this as crew, rather than on your own boat? If so, then you will want to get up to speed with your skills as soon as possible. Frankly, not many owners will be interested in taking on unskilled crew for big passages. Local sailing clubs and schools will offer classes
. After you know the basics, then get general sailing experience however you can -- offering yourself as rail meat to racers isn't a bad way, so long as you have a thick skin and are willing to learn.
There are various crew finder websites, and CF also has a sub-forum for people looking for/willing to, crew. Often, hanging around at the docks can be a good way to snag one, too. Delivery
skippers and companies will sometimes take on less experienced crew. While there are bigger companies that specialize in this, I'd suggest googling for local delivery
skippers as they are more likely to give you a better experience. Don't expect to be paid, though!
Do you know whether you're sensitive to motion sickness? Not that sailors don't get it, too -- just about everybody has, at least in certain conditions, but there are some, few people who are very sensitive to it and have a real problem getting over it. If you're one of the unlucky few, best to know that before you commit yourself! Two or more weeks of utter misery will be hazardous to your health!
Good luck to you, and CF is a great place to ask your questions.