done it numerous times
Harbor hopping is fine, but my advice is that if you've got a great weather window, don't stop, or at least don't stop short of Monterey.The worst section, despite what Southern Californians will tell you about Point Conception, is from Morrow Bay to Monterey. What we usually do there is take a short hop up to San Simeon and drop the hook in the cove there, cat napping until the wind dies around 2100. (Don't try this with a southerly swell.) Then, we blast all night to Monterey, arriving around 1000 the next morning. (I'm assuming here that your 41DS will make the same speed as my former 410 made.)The other consideration is that you might want to bypass Santa Barbara, opting to anchor at Cuyler Harbor on San Miguel island instead. It can be a nasty anchorage in the wind, but if things are nice it somewhat takes Point Conception out of the picture. You need a real good forecast to do this, and realize that if the swell turns nasty there's a good chance of Morro Bay shutting down because the harbor bar will be breaking. (Alternative is Port of San Louis in a pinch.) ALWAYS contact Morrow Bay harbormaster on VHF before attempting the bar.If you're harbor hopping this time of year, realize that night landings in Santa Barbara and Monterey can be tricky, especially if you're unfamiliar with those harbors. In Santa Barbara if feels as if you're going to hit the beach before you make the turn, and in Monterey it will seem as if you're going to crash right into the wharf. Local knowledge is a good thing on this trip.Point Sur is often the toughest bashing, although we once sailed smoothly in early July around Conception, Arguello and Sur only to be stopped by Point Ano Nuevo off Davenport. You never know. I've done the trip southbound once in November and northbound once in December, and you're better off attempting it in October. The shorter the days get, the longer the nights. Fair winds. And let us know what name the new boat will go by. (Our h46le is "Bashful," by the way, in Redwood City. I'm sure we'll bump into you sooner or later, especially if you're a member of Coyote Pt. YC.)