There's good advice posted here, I don't mean to contradict any of it. I hope this will add some to what's already posted.
I've made the round-trip
passage, Pillar Point -> Santa Cruz - Monterey -> Pillar Point, in a 26 foot
Pearson Ariel several times. My most recent return from Monterey to Pillar Point can be seen here:
Google Maps APRS
A few cautions:
1) Expect the winds to be
twice the
forecast around Pigeon Point. The prevailing winds there are out of the north to northwest, and if the swell is out of the west, the combined wind waves and swells can produce cross seas with no favorable point of sail to avoid a
capsize. I spent several hours one evening hove to with a
sea anchor under bare poles in 40
knot winds and 12 foot combined cross seas that I will never forget - because I sailed too close (3 miles) to shore when the thermals kicked in in the afternoon. I floated weightless in the
cabin at times, and there wasn't a surface in the
cabin that I wasn't slammed against at least once.
Give Pigeon Point lots of sea room - stay 20 miles offshore if the winds are likely to kick up. If you see lots of spray kicked up to 500 feet as you approach Pigeon Point, beware!
2)
The best time to depart Santa Cruz for Pillar Point is 2 to 4 AM. Trying to go around the bend northward toward Ano Nuevo in the afternoon is likely to get you caught in a
washing machine of high winds and seas created as the northwest wind turns the bend north of Santa Cruz. Expect fog leaving Santa Cruz.
3)
Marine weather forecasts generally suck. As a pilot, I'm spoiled by the much more accurate forecasts for pilots. I determine my own
forecast by consulting the
Pacific Briefing Package. For local
weather at Pillar Point, I consult the Half Moon Bay AWOS at: 650-728-5649. It's continually updated. Listen closely for the temperature and dew point. If there's less than a 2 degree C spread, expect fog.
From the map linked above, you'll see my track from Monterey. My plan was to leave Monterey at sunrise (in fog) and try to beat the mid-day winds at the bend north of Santa Cruz. It didn't
work. I got caught in 35
knot winds and 8 foot windwaves with no prospect of beating upwind while taking those waves abeam. After having a few windwaves board my
cockpit over the side, I turned tail back into Santa Cruz. I left early the next morning and made the
passage with easy sailing conditions.