I made this trip in November last year and had a fine time. Unfortunately, I arrived after dark, which I do not recommend. It made for an "interesting" approach. And when I left the next morning it was foggy, so I never really saw much of Half Moon Bay. But those things aside, here are some notes:
1. Watch out for crab pots (as marked by brightly colored floats) going down the coast. In crab season, they are all over the place and you will want to avoid getting too near them to prevent the possibility of having lines tangled in your prop.
2. Avoid the shallows marked on your chart. Don't be tempted to make a shortcut -- stay outside of marker G1 and go in between G3 and R2 before turning north toward the entrance to Pillar Point Harbor.
3. Be prepared to encounter swells coming from the side as you approach the harbor.
4. If you anchor in the outer harbor, as I did, give the harbormaster a call to let them know you are there. They will appreciate it. There is no cost for anchoring, but they like to know who's out there.
5. If you get a slip in the inner harbor, you can make arrangements with the harbormaster in advance.