Sailing the Caribbean for the First Time.

[s/v Breakaway]

Freyman, here is a perfect example of what I had in mind:
30 ft ticon sloop 1984

It's a Ticon 30, built in Canada, currently located in St Thomas, USVI. I know nothing about this brand of boat, but to me it looks perfect for your plan. It's asking price is $9000 and appears to be in good enough shape for 6 months use in relatively protected waters, assuming the hull is sound. There's a fair amount of info on the internet about Ticon 30's.