Welcome to CF!
If you are brand new to sailing... you have a great bay to learn on. If you have experience already, then I would say to practice overnight or night sailing in Southern Cal
. Do a triangle sail. San Diego
to Dana Point
and back down to San Diego
or the reverse. You will gain experience with upwind, downwind, no wind
I lived in So Cal
before heading south for good and I did the trip to Cabo and back a number of times. Single-handed and with crew on my boat and also helped bring dock
buddies boats both south and north on first time trips.
Yes... there is the "Ha Ha" and from what I hear and have seen, it is a fun party and huge group sail, so that may be for you. Personally, from my observations of the Ha Ha fleet leavings and arrivings over the years, I just compare it to very bad rush hour traffic on the freeway. Nowhere I choose to be. But for you, the crowd may be a good first time hand holder. Your call.
Practice where you are first. Gain confidence doing night sails
in So Cal then... let 'er rip southbound!