sail carribean single-handed for one season?

[Suijin]

1. Buy a boat in Ft. Lauderdale. Flights there from Boston are cheap. Be there for the survey. It will be money and time well spent.
2. Cruise the Abacos and Exumas. Plenty to see, it's like training wheels for the actual Caribbean. And you can easily get it back to the US for storage/resale.
3. If that works out you'll find a way to move the boat south.

[Exonerated]

Avoid buying a boat if possible. I would contact sailboat charters in the BVI‘s. You should be able to work out a long-term charter. I would do it by the month with the right to extend. I suggest that because this dream could last six months a lifetime or 30 days. After 30 days experience in the BVI’s the charterer may expand your sailing grounds to PRVI or St Maarten or beyond.

gulfcoastsailor--

I love the idea of not buying a boat, but a month in only the BVIs doesn't sound ideal, especially with only the possibility of roaming further. Especially since the BVIs will be one of the few places I've gotten to experience already through week-long charters.

If I could find some more flexible arrangement from the start, then not buying would be great. I'm just not too optimistic about finding anything satisfactory.

Also most charter fleets are much nicer and more expensive boats than I need for this.