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My wife and I have been talking about doing this before potentially having kids so it is a bit of a life goal thing. We also aren't averse to returning to work if needed and things don't completely work out.
I've also looked at potentially earning some side income and believe that even part time work could sustain us for quite some time.
I agree with others that you probably don't have enough assets IF you plan to retire permanently now. From this followup post, however, it looks like it could be more in the way of a sabbatical? How easy would it be for you to return to work/income?
Another question would revolve around your wife's age if this Caribbean sojourn is seen by the two of you as something to do before potential kids. If she is exactly your age, you probably don't want to delay the sailing while waiting for the RSUs--non-interventional fertility is not helped by putting things off in one's thirties--especially after 35.