I am a sailor (long-time first mate to my husband the life-long sailor) and believe me when I say that you don't learn to sail by signing on with a charter or something. You need to go out with some recreational sailors a few times to make sure you don't get sea sick, make sure you don't go stir crazy and make sure you actually like it. There are many folks who look for EXPERIENCED sailors to help sail a boat south for a season (there are businesses who do this) but no one in their right mind hires a person with no sailing experience. I'm assuming from your message that you haven't actually sailed or have done so only occasionally. There's ALOT to learn. So go sailing from home with friends, hang out at boatyards and volunteer to help in exchange for a few sailing trips, take lessons, etc. Otherwise, come to the VIs on vacation and sign up for a bunch of the charters. HOWEVER, we have sailed off STJ a few times and the winds are frequently light which makes it very challenging to learn. Other times, its been great. The VIs are a wonderful place to sail because its fairly predictable (unlike good old Buzzards Bay off Mass) but you need some wind and a good teacher who is patient.
If you are trying to "get to the VIs" there are a million other ways to get here (bargain plane tickets and camping) but once you do learn to sail, and can put your experiences on a resume, you could get yourself hired as a cook on a boat being moved south which is its own experience (how to get along in VERY close quarters with virtual strangers for a long period of time, depending on where your sail starts from). Good luck, you have much to experience!

jorja,
there are many sailing schools on the east coast. normally a week or two, sometimes a couple of days. most people i know went to a school in anappollis (sp) Where the naval academy is. buy yourself a sunfish or some other small one man boat. also i believe the coast guard gives a course every so often. get your feet wet and good luck. i just remembered i think the naval school is for a weekend.

One Love ironman

thank you for the reality check! that's as I suspected. =).

I talked with a guy named Captain David Kummerle. He is from St. Croix and charters his boat out of both St. Croix and St. Thomas. His boat is called Glory of Christiansted. His charters are for learning how to sail.
He taught basic and advanced sailing/cruising for Annapolis Sailing School and managed their St Croix school for 2 years.

He is friends of our local librarian and I've sent him a couple of emails about my trip. Check out this web site.
http://www.inthewild.org/glory_sailing.htm

Don't give up on your dream so easy. Carpediem!