Scotty's perception of Cojo and San Simeon and Pieffer is spot on. Even with a west/northwest swell San Simeon is not exactly trouble free. Even though a long time surfer and having lived along the coast of SLO County for over 30 yrs (thereby possessing very good knowledge of this coast) I always maintained an anchor
watch at San Simeon. Mostly, I would just not bother with San Simeon. At San Simeon either tuck in close to the lee of the bluff nearest the beach where there is deep water
and good holding or stand about straight out from the pier but as close to the pier as you dare. Otherwise, stay outside the bight formed from the point to the end of the pier.
Standing off when rounding Conception is the ticket. Inshore from Conception to Pt Buchon (just northwest of San Luis Bay) gets lumpy and puts you in the littoral current
. Plus, remaining inshore between Pt Arguello and Pt Sal may get you a visit from the USCG because of proximity to Vandenburg AFB and space complex. It may be whisper jet, helo, or RIB
. They may just tell you to head
out hich you should be anyway. When approaching Morro Bay from the south stand off about 6 nm because it gets quite lumpy and light, flukey, or back winds at Buchon, Diablo Canyon and almost to the harbor mouth.
From the town of Cayucos (6 sm north of Morro Bay) to Point Estero there is a rock reef which extends west of Pt Estero. You'll want to stand off 4-5 nm at Estero thence perhaps around 3 nm until north of Piedras Blancos. However, there are many wash rocks waiting for the unsuspecting mariner until north of Pt Sur.
Definitely closely watch the weather
when approaching Pt Sur. I too have seem some very wicked weather there.
HMB entrance can be tedious but for good reason. As noted by others, there are rocks. Maintain a close watch until inside the breakwater. Two times it was surging off wash rocks at low tide and a big swell.
(Side note: I do believe HMB harbor was constructed by the same concern that built the harbor at Dana Point
. It languished for well over it's first decade of existence. I was struck by the seeming stupidity of a recreational harbor ala Dana but in NorCal. Maybe it's a going concern by now and more than a waypoint for transiting sailors. A nice town with a harbor problem.