Cruising the US Pacific Coast
Should be a pretty good time to do it weather-wise, all downwind, as long as you avoid going when a late Southerly is blowing.
The problem with most anchorages and harbors along Washington and Oregon is that the only time you CAN''T get in to them is when the weather is really bad. The coastline is pretty unforgiving in big seas, so its usually best to just run with it. You can always get into SF Bay, and south of there is rarely a problem, as all the harbors are all-weather, except Morro Bay in extreme cases.
If its your first crossing to Hawaii, you might consider joining up with a race, even if you don''t really compete. They make you have all the safety gear, do twice-a-day radio and position check-ins, track your progress, and you''re traveling in the comnpany of a few dozen other boats. On top of that, its fun! TransPac from L.A. in odd years, Pacific Cup from S.F. in even years.