Out the Gate, down the coast, around Conception, and the bash home.

Down is the easy half: Half Moon Bay, Santa Cruz, Monterey, the long Big Sur leg to San Simeon, Morro Bay, then the wait at Cojo for a window around Point Conception. After that it's the Santa Barbara Channel, Santa Cruz Island, and a mooring at Two Harbors with the water a color it has no business being.
Back is the sail. Wind and swell on the nose from Conception to the Gate. You day-hop the harbors, leave before dawn, and take calm windows when they come. Everyone who has done it says the same thing: don't sail to a schedule.
“We decided to do it in day hops only, waiting as needed for either calm or favorable winds.”Latitude 38, sailing north from Santa Barbara
Roughly how it goes, from the people who have done it. Numbers to be corrected by weather.
| when | what |
|---|---|
| Days 1–3 | Golden Gate → Half Moon Bay → Santa Cruz → Monterey. Short legs, shake the boat down. |
| Days 4–5 | Monterey → San Simeon, the Big Sur overnight. → Morro Bay. |
| Days 6–7 | Morro Bay → Cojo. Wait for Conception to lie down. |
| Days 8–10 | Santa Barbara, Santa Cruz Island, then across to Two Harbors. |
| Days 11–12 | Catalina. Avalon for the ice cream, Two Harbors for the quiet. |
| Days 13–21 | The bash: Cojo, Morro Bay, San Simeon, Monterey, Santa Cruz, Half Moon Bay, home. Pre-dawn departures, calm windows, no hero moves. |



Three weeks in late summer with one other person who is good company at 4 AM. Charter a forty-footer for a couple of weeks; the families fly in and join for the easy leg, mainland to Catalina and back. Then the two of us bash home, which I get to complain about for years. (A pal's amendment, on first reading: the real move is to sail back via Hawaii. Noted.)
Other people's accounts and the official pages. Read these before believing anything above.