Leaving the city life...

[CottageGirl]

Sounds like an awesome plan!
I would (respectfully) disagree with sailing charters in the BVI's. Perhaps consider sailing school in the BVI's. After you live, learn (and work) on a boat for a week, you're going to get a pretty good idea of whether the sailing life is for you. We took our ASA 101, 103, 104, and 114 on a 47' catamaran in the BVI's over a 10 day period. It was the most exhausting, but empowering, thing I've done (I'd just turned 50 when we "went to school"). IF you're going to take any sort of vacation over the next 3 years of prepping, consider live on board sailing school.

Plus, you WILL fall in love with the islands and it'll make you more determined to realize your dream :-)
Best of luck!