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Answered 2015-07-15 19:01:03
Not sure about the sail down, but the best time to come back, in theory at least, is at the end of April or the beginning of May, before hurricane season.
I'm not sure how far into Mexico you're going. But I'll assume you're going as far south as Cabo San Lucas or further (which is sort of the top edge of the Mexico hurricane zone).
Hurricanes run from August to late November. So for added insurance, wait thirty days after hurricane season. So the earliest you should be thinking about leaving Oregon is around January 1.
Expect the ride back to be rough. As you're probably already aware, it's uphill sailing (against the wind and current) the entire way.
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