You can get a lot of expierence sailing on San Francisco
Try hooking up with the various Yacht Clubs and get on as crew in the Beer
Can Races... There is a race
almost every day in the summer...
In the East Bay, I recommend, Berkeley Richmond, Encinal and Oakland Yacht Clubs... Their members are friendly and new crew is always welcome.
It sounds like you are taking lessons through a US Sailing Club, so I'll assume you are either at OCSC or Club Nautique... Take as many classes
as you can afford, but experience is the best teacher. Both of them have charter
fleets and crew lists so you can split expenses with other members. They also organize charters to fair away places and it would be worth going along to see if this life is for you...
Lori and I left San Francisco in Sept. 2010 and have not looked back. There is a big world out there and with a little perseverance you can do it to....