Sorry, but when I replied earlier in this thread it did not occur to me that Alameda is actually in San Francisco Bay (rather than somewhere in the greater LA area)....... I sailed the Channel Islands area for quite a few years and although never having to go North of Point Conception myself, studied weather developments in the Pacific very carefully in connection with Rivendel's ssuccessful passages to Hawaii ('94, '97) and the Sea of Cortez ('93 and '95).
This has taught me (the hard way) that pilot charts and other forms of historical weather data are pretty much useless unless the ENSO (El Nino vs La Nina oscillation) status is pretty close to neutral. Currently, we are in a moderately strong El Nino phase. As a result, one may expect the relatively late establishment of a relatively weak Pacific High.
This can be important because the steady procession of strong depressions spinning off from the polar low tends to penetrate further South than when the West coast of the USA is being protected by a large, strong Pacific high.
Even under favorable ENSO conditions the Pacific High tends to establish itself sometime during the Spring. This is one of the reasons that Winter passages up and down the W Coast are generally discouraged. Only a few weeks ago there were horrible weather conditions along the Northern part of the coast that resulted in the loss (with all hands) of a large catamaran, as most of us do probably remember. So, in most years, longer coastal passages are best made in May or later. In an El Nino year, however, it may well take till June or July till the risk of marauding low pressure systems diminishes significantly.
In short, I would keep a keen eye on the establishment of a stable Pacific High before planning to leave. When getting ready, make sure to plot the 5-6 day FNMOC wave and wind forecasts, as the low pressure system that might be threatening you 4 or 5 days from now is almost certainly already in existence way up North and current prediction models often do an amazingly good job of predicting its trajectory. Here is an impression of the highly informative format of the FNMOC EastPac 0-144 hr wind/wave forecasts
(just click past the security certificate warning typical for many DOD sites).
Finally, I would strongly discourage trying to make the trip shorthanded as fatigue is the single most dangerous factor on these type of long coastal or near-offshore passages.
S/V Rivendel II
Port Vila (Vanuatu)