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There's an entire strata of Great Lakes skippers (like myself) transiting to ocean sailing who want logged hours to qualify for RYA certifications or equivalents so that they can charter or go south themselves. I think the difference between serious heavy weather on the Great Lakes or coastal Maine/Maritimes is duration and swell: 60 knots here is nasty anywhere, but it never lasts long on a big lake (40 knots can last all day in the spring and fall, however).
So if you are very clear about YOUR qualifications, the safety equipment aboard, the expected duration, and your willingness to work with and not over a potential crew (while acknowledging that the skipper has the last word), I think you could get someone to do it for the plane ticket return price easily.
Hell, I paid my own way to Portugal and back to spend two days in weak weather on Giulietta; 10 days in November offshore would be far more helpful to my ambitions!
The biggest issue, of course, is finding someone who can free up an indeterminate block of time, subject to weather, etc.
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