Pretty much agree with svHyLite.
There are lots of sailboats in San Diego and lots of sailing going on.
On San Diego Bay and out past Pt Loma into the open ocean.
Winds are generally light, 15 knots is usally a lot of wind here, but of course
it does higher on occasion.
There are few places to anchor for the night or a weekend in the bay and you can also run up to Mission Bay and anchor there.
San Clemente Island is 60+ miles from San Diego, controlled by the Navy so the anchorages are shut down from time to time. Seems to be more frequently these days.
Santa Catalina is a bit further.
Ensenada to the south provides the first protected anchorage as well as as marinas to check into if desired - ~60 miles south of the border.
So weekend trips are limited.
But active racing community, beer can racing on Wed in season. And the weather is good year round.
Marina space has opened up the past few years. So getting a slip is not the issue it was a few years ago. I think all the marinas have open slips in most sizes. But slip rates have not come down.
Crazy Fish - Maintaining, Upgrading and Sailing a Crealock 37