Grosso, sounded like fun to me too. I haven't been up there in a sail boat but have done a lot of diving there on the dive boats out of Santa Barbara. I went up there one day and before we left the dock it was cloudy and drizzling. Not much wind. Was awakened around 6 AM and went up on deck to find we were in a gale. It was quit pleasant diving on the lee side of the islands however. The spray from the waves was going over the top of the 85' dive boat on the way back. I know even in the summer it can get rough out there, especially around San Miguel, very fast. What starts out as a warm sunny day can end in small craft or gale winds by afternoon with 12 - 18' seas.
It pays to keep an eye on the weather reports if you are going. I am hoping to take a week next year and make a stop or at Catalina then Santa Cruz on the way to Ventura.