Go to North Beach, check out Spectacles + City Lights bookstore. Grab a pizza at Tonys (sit at the bar), then walk it off up to Coit Tower.
Bart to 24th in the Mission, wander down 24th St and grab a coffee at Haus on corner of Folsom. Find a taco joint for $1 tacos. Climb up Bernal Heights then drop down into Courtland Avenue for a beer.
You will find your weird shit in the Tenderloin. SF is perhaps the most depressingly Dickensian city in the world. Before seeing it I'd never imagined a city with so many billionaires would let its residents suffer so.
The past few times I went for an interview to a new location, I first went to a meetup / group. Asked folks (who have lived and have no stakes in your interview) what they like and don't like. Also, walked few blocks around interview spot in the evening and morning for as long as I could to get a better feel of the area.
Cafes: Caffe Trieste (North Beach)
Restaurants: The Ramp (Dogpatch), Sunday morning brunch at Thai Temple (Berkeley), Fish (Sausalito)
Sights: Twin Peaks, Coit Tower, Berkeley hills (Grizzly peak)
Weird shit: The Saloon (North Beach), Ruby Room (Oakland), parties at 20 Mission (Mission), Li Po Cocktail Lounge (Chinatown)