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Macroscien said..Mastbender said..
Been lurking here for awhile, from the USA, finally joined, so I could respond to this thread.
I was born and raised in San Diego, and it sucks for wind, kites maybe, but for windsurfing, pfffft.
Happy trails.
Just in case I want to try, If San Diego Bay is free to sail or any restrictions for windsurfers ? Looks nice 2 km across at least, maybe on bigger board ? Is it clean water there ?

What is shown as San Diego Bay in that pic is actually mostly a Military harbor, Navy mostly, with restricted areas which are even larger ever since 911. The water quality can be a bit iffy in areas, many large ships that can bring their own variety of stuff. The harbor has only one entrance to the ocean (Point Loma) so the water doesn't get that good of circulation.
Mission Bay, just to the north (between Mission Beach and Bay Park, on your first map), is more sail friendly, you can sail anywhere, windsurfers favor being out in front of the Hilton Hotel on the east side of the bay, but you'll need a very big board and a very big sail to even get going.
San Diego is famous for it's sail regattas, America's Cup and all that, but we're talking big sailboats, which is a far cry from windsurfers.
I fear you'd be disappointed, but San Francisco is a slam dunk, you'll get blisters from sailing so much.