Joel,
Wow, there is a ton of stuff to do.....
For sailing, Try
Modern Sailing in Sausalito, they have a good solid charter fleet. ALX!!! have you seen this, Maybe a boat ride??? Our own Alx has a J-30 right on the water front at Pier-39. Great place to start from. Let's torture him into taking you sailing.
In fact, expect to spend a 1/4 day walking around that little village. The main town marina is a fun place to walk around. Great Mexican food at Salsalito (sic). Fabulous high-end food at Sushi Ran (the best sushi in CA by multiple surveys, but not cheap).
Plan on heading out to the Marin Headlands to see what the coast looks like, and if you want "funky" you can drop in on the town of Bolinas. Crazy-town but funny.
As to hotels, I need more info. There are zillions of places, but they are all pretty expensive. Some have water views, some are in interesting neighborhoods, some are in dangerous neighborhoods. One of my favorites is in Pacific Heights. Which is a very high-end residential neighborhood which doesn't have anything to do but is very very quiet. Let me know more about what you're looking for.
Get a Clipper Card if you're spending time in the city, you can hop on-n-off of the busses and subways etc... and not worry about parking. Parking is a BIG hassle.
There is a ton more, but I need more guidance on style and budget. The SF Bay Area isn't one of the top four tourist destinations for nothing.

Cheers,
B