We bludgeoned our way north from San Diego
to San Francisco
this Dec '07 - Jan '08 in our 33' sailboat. Due to prevailing winds, those huge systems that kept coming through, we chose to harbor hop north the whole way vs. go far out and get smacked by some of the monsters that came through this year. Dec 24 to Jan 19 was our timeframe, and we cowered in some of the finest harbors I've spent time in as systems swept by. The big move (Santa Barabara to Monterey) was the most committing in terms of needing a clean window ---- we didn't have the weather
or swell conditions to either anchor
at Pt Concepcion or enter Morro Bay or anchor
at Pt San Luis........so we just budgeted for the big move. We ended up getting hit with wind
(30+ kts) and swell (10-12') off of Pt Sur and spending about 24 hours longer out there than budgeted, but it all worked out careening our way into Monterey. Making harbor there at dawn was the best accidental mistake we made (we had though that we could come in during darkness and anchor outside.......not so, it turned out).
All this said ----- heading north out of season up the Pacific Coast, even in a sound boat with solid crew is just a workout and not particularly fun. I was thankful that, unlike the delivery
crews we saw (who seemed to be the only other sailors out there!), we didn't have a sense of schedule or get-there-itis.........which seems to drive most of the bad situations and decisions I've made or heard about.
Heading further north from here (San Fran) I think we will look/wait for that nice window of April/May of whatever year we head