It depends. Mexico is bordering San Diego, so your trip can take a few minutes or several days, depending on route and weather conditions.
Rough Sailing - 1923 was released on: USA: 13 November 1923
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.
same
Rough RNA.-- Lucas J. Ammons
The sailing vessel Mayflower was headed for Virginia, but due to poor navigation and a bit of rough weather she ended up in New England.
rough
The Sierra Madre mountain ranges.
The seas can be rough in December when sailing in the Caribbean because its Hurricane Season. Most Cruise ship will have to sail through rolling seas at some point, but they do shy away from the major storms.
It is crusty and it is very rough and it is very bumpy and has alot of holes in it
Any ocean in the world. The Bering sea, Atlantic and Pacific can be very rough.
most of the days were rough with rainstorms while he was sailing and other days were calm and peaceful