Spend the
winter in
Hawaii, getting to know the
boat better, and making sure the two of you are comfortable with
living aboard. Then tackle the crossing the next May or June, when the No. Pacific high settles in. It will be two to three weeks to SF or points north, depending on where the high is, and you don't want to be heading S along the No. American coast until then anyway. In fact, you might want to
head for the Strait of Juan de Fuca, spend the summer in the islands north of the Strait, and then
head S in say August or September. Cruising is about going with the seasonal
weather patterns, not fighting them, as you may do in an October crossing from Hawaii. I did a Hawaii to Strait of JdF crossing in July a few years back, and it was an idyllic 3 1/2 week sail in a 42' sailboat. I have no interest in being out in the middle of the Pacific in months when storms may hit, and October is questionable.
As for spares, there are threads on this Forum you can search, and any number of books on cruising with recommendations on the topic. I sail a junk rigged
boat, and the main thing I need at sea is more line in appropriate sizes to replace lines that chafe during a
passage. You can go stock up on anything that might fail, and your lockers will be filled to overflowing, or you can be more conservative, recognizing that you are facing a 3 week voyage and will be able to replace anything that breaks once you get there. Just make sure the rig is in good shape before you leave, and have backups for your
steering system so you don't have to spend the whole voyage sitting at the
wheel. I have an
autopilot and a
windvane, so two systems have to break before I become a slave to the tiller. So far, these two systems have not failed me. (I would knock on
wood, but the boat is
steel ...)