Re: Sailing up Coast of California
We did this trip in July 2011, we took a small 1985 Catalina 27 from the SDYC in San Diego to the Oakland Yacht Club in Alameda, in the heart of the SF Bay.
We had a crew of three at all times, four for some specific legs of the trip.
My main recommendation, look for a time/weather window where the Pacific high has been active for a few days (and located somewhere between SF and Hawaii) and is forecast to be for a few more. This will bring fog to the CA coast and light winds as pressure between the inland valleys and the Pacific ocean is equalized. Under these conditions you may find days of very light winds along the coast.
Our trip took exactly 7 days and we overnighted in Ventura, Morro Bay, and Monterey. All the other nights were spent at sea. We crossed Pt Concepcion early in the morning under thick fog and glassy conditions. We then hit rough seas from Morro Bay all the way to Monterey, and then on from Monterey to Half Moon Bay. Prepared to beat up against the wind under engine power and to get very wet (at least on small boats like ours). We had a single-reefed mansail up almost the entire voyage, it really helps stabilize the boat against the wind.