I.ve made the trip in both sail and power.. the area you're looking at in boats is a good one.. (by the way, if looking, I cant say enough good things about "Nina" at Delta Yacht Sales at OxBow Marina, One of the rare ones thats honest and up-front when buying
a boat, .. and while there, stop in and say "Hi" next door as I own the Canvas
As far as the trip south, you should'nt have any issues.. I've got a couple guides for traveling down the coast and you're welcome to them..
If It were Me, I'd take advantage of the trip and stop overnight in port, not as much to get off the water but to experance the the ports
from the water side..
Half Moon bay (Princeton), Montery, San Simion, Morro Bay, Port San Luis, and Santa Barbara........ they are all good stops and a different prospective when staying in the Marinas
and traveling the open ocean.. you've probably had rougher water crossing San Pablo Bay in a tide change... spring and fall are your best times to travel.. the winds build in the summer months in the afternoon, like SF Bay
and the waves build a bit.
And winter being about the best time, as the water is flatter (between weather
fronts) but you could be trapped in a harbor for a couple weeks wating for another window. uasally you'll have a window of a few days..
Personally, we like traveling the coast in the winter, its crisp air, and you dont have to deal with the damn fog
good luck in your adventures