I used to deliver along this coast so have made the trip dozens of time. First decision is whether you want to dawdle along with multiple stops as you go, or get to PNW ASAP. Fueling of course may need to get factored in, and your comfort with running at night.
Central coast is more or less Pt Conception to Cape Mendocino. Typical weather in June is almost always winds from NW-NNW though intensity and duration varies. Typical is for the wind to start late morning and build through the afternoon to 25-30 kts. At around 17 kts of wind, small whitecaps start forming. If you see these earlier than about 11, you're probably in for a long day. That said, not unusual for early morning gusts to come up - I recall getting slammed by 45-kt sustained easf winds off Pt Reyes one morning that had me seriously thinking about ducking into Drakes Bay, but they only lasted 5 nms or so - a really localized wx pattern I suppose. But for the normal pattern of afternoon winds, you can knock-down a lot of the seas by taking the beach route - tuck a mile or two off the surf line during the day when visibility is good. At night, drift off 5+ miles into deeper water to avoid crab pots (if your boat doesn't have line cutters in the shafts, recommend you install).
Vast majority of my trips were nonstop as I was delivering strong boats. I happen to enjoy running at night despite the fatigue of standing dog watches. Three people aboard makes for a decent watch schedule - I liked a schedule of 2-hr at night, and two 3-hour daytime watches for each. I also like to keep the same schedule for the trip vs rotating the worst watch.
For SoCal boaters making this trip the first time, a big decision seems to be whether to stop at Morro Bay. Coming from San Diego may mean you need fuel. I rarely stopped because the tides and currents need to be timed which would be disruptive on a delivery. It's a pretty long run to Monterey without any decent anchorages (San Simeon is an open road stead so fine for a rest in decent weather, not a great place to ride out weather). Although the coastline looks pretty straight, for some reason I always seemed to get slapped a bit around Pt Sur and Cape San Martin.
Make sure everything is well secured on your boat, especially for overnight runs. At night, everything is amplified. What was rattling dishes in a cupboard during the day sounds like crashing glass at night - a mental thing, but makes for a long night. Anything on deck needs to be secured with compression straps or cables with turnbuckles, not just rope and knots. I'm not trying to scare you into thinking you'll encounter Perfect Storm conditions,, but after dozens of hours of banging into chop and constant wind, lines and knors slowly loosen. What worked in the protected waters off SoCal will not work for long duration of open ocean running.
Seasickness. It's a personal decision. Because I was delivering, I was often running short handed - often just one crew and myself (I was much younger then). I would often take a half-dose of meclazine as a prophylactic. Seasickness medications work, but have side effects. Half dose walked a balanced mine for me.
There are guidebooks written on this trip that are still worthwhile despite their age and the advent of Active Captain. Don and Rayanne Douglass book by Fine Edge is a great book, and I prefer it to the Brian Fagan book.
But what all the prep and reading can't decide for you is what do you want the trip to look like? Delivery or dawdle? How do you feel about running at night (can be mitigated, but difficult to avoid entirely)?
As far as weather, there is always - always - a small craft advisory posted along the coast (only a very slight exaggeration). You will, within a few days, start to get comfortable with correlating the weather forecasts with what you're actually seeing. For the most part, during this time of year, weather can be chunked into 4-6 hour blocks meaning the lousy afternoon chop doesn't usually build until 1:00 or so, crests around 4-5, and dies down by sunset. As mentioned, taking the beach route (if you're comfortable with it) knocks that down considerably (I'm sure someone will chime in about deep water being better - simply is not my experience, but each captain makes his/her own decisions).
In closing, while Pt Conception deserves respect, in my opinion, SoCal Sailors fear it too much. It carries the same fear that going out the Golden Gate does for San Francisco boaters.
Good luck and please consider posting trip updates to this forum - many armchair Sailors who would take vicarious delight in your travels
Peter
