We sail the Bay 12 months per year...(pull the boat for paint in August when prices are down). Although it can be cool, it can be in some ways the best time. Bring a coleman stove to take the chill out of the cabin...and tow a fishing line because Oct & Nov the big Rockfish (stipped bass) head south. If the weather gets bad along the way, there are plenty of places to pull in for a couple days. You will also have a higher likelyhood of North to Northwesterly winds to push you down without having to tack. Of course if the wind is out of the south, it'll be a little warmer, but nonetheless, all sounds like a great time to go.
Chris Craft Apache 37 Sloop (S&S)