Kathy and I made this trip, and then some on to Santa Cruz and Monterey. On advice from my very experienced coastal sailing brother I evaluated three major obstacles.
1. Take the ship channel well past the shallows outside the gate before turning south. Ditto for the return. Bend this rule a bit if you have a sound understanding of how wind and tide affect these areas. They are deadly.
2. Be sure the period between waves, in seconds, exceeds the height of waves and swell in feet. We came home at 8 seconds and 8' which emptied the cupboards without landing a drop of water on the deck! You will likely have the swell on the stern going down and quartering on the way home. The boat can take it better than me. But, I would not go again in anything worse.
We had 1/4 mile visibility coming home and in the ship channel. AIS and radar were great. If you can, set up your radio, or perhaps your hand held, so you can monitor both 16 and the vessel control channel.
3. There is a shallow area well marked on your chart for coming and going south of Pillar Point, the harbor you will likely use. It should not come into play from the north.
We loved the challenge of this trip and the subsequent name dropping. Wait for the right weather and do it!