Is the geek sailing trend recent, or just something I'm only noticing being out in San Francisco right now? It's coming up in almost every group I hang out with; they've got time shares, they're going to sailing class. Is this what "we" do now?
I don't know about recent, but sailing is awesome! We do it quite a bit here in Marblehead. As this year's commander of the Marblehead Sail and Power Squadron
http://www.usps.org/localusps/marblehead/exec-comm.html
I would whole-heartedly encourage you to take a boating safety course and learn some basic stuff before you go get too adventurous!
I thought kitesurfing was the new geek trend. Read a bunch of articles about a bunch of Google bigwigs taking that up a couple years ago. I'm still too chicken to try it, alas.
Where do people go for sailing class in SF? I sailed in college and am looking to pick it up again...
I'd love to get into that, but given that my only sailing experience is 420s and FJs on a lake that never had any wind, I think I should probably start with something a little less hard to handle. ;-) Know of any dinghy sailing schools in the South Bay?