get a good cruising guide
In the early 90's we used to cruise "Rivendel II" (Legend 43, hull #1)out of Santa Barbara and visited San Diego plus Catalina many times, as well as the NorthWestern island group (Anacapa, Santa Cruz, Santa Rosa and San Miguel). You probably don't have time to go all the way to San Miguel (roughest weather because of vicinity to Point Conception, but most beautiful beaches and large elephant seal colony). Try to visit Santa Cruz, though since it has a number of great anchorages (Pelican Harbor, Fry's, Bluebanks) and can be visited with a permit (wonderful hiking).There is much to learn about the weather and about the shipping lanes, so get yourself a good cruising guide and chart book. Next time you have a week to sail out of San Diego you may also want to consider going South and visiting Ensenada in Mexico (with an incredible anchorage or two in the Todos Santos island group).When leaving San Diego harbor and going North, don't try to shortcut around Point Loma (because of kelp and obstacles). Just follow the buoyed channel almost all the way out before turning North. The nights are going to be cold, Make sure you have some means of staying warm.Have fun!Flying Dutchman