Arrive at Oakland International Airport and follow the signs for taxi stands, which are located on the center islands outside of Baggage Claim on all levels. The taxi will cost about $50, and you'll get great skyline views of the city as you cross the Bay Bridge. You're headed to The Scarlet Huntington Hotel in Nob Hill, one of the chicest addresses in the city, and once patronized by luminaries like Lauren Bacall, Picasso, and Pavarotti.
Allow the award-winning staff to attend to your luggage while you walk south toward Hayes Valley, taking in spectacular views as you descend the hill. You'll have Huntington Park, Grace Cathedral, The Fairmont and the Nob Hill Masonic Temple to gawk at when you start your walk, but there's plenty of architectural eye-candy to be had along the way as you pass from Nob Hill through Union Square and the Mission.
Next up is brunch at Zuni Cafe, a must-see for any Urban Specialist, and one of the most revered restaurants in the city. Chef Judy Rodger's market-driven menu has made her famous, and when you try her brick-oven-roasted whole chicken with Tuscan bread salad you'll understand why. The crowd here is both gay and straight, but is always congenial and high-energy. Grab a seat at the bar and you'll be sure to strike up a conversation.
After brunch, it's time for a spot of shopping in the gay district of the Castro, where stores selling men's designer clothing and upscale home accessories mingle with used record stores and kitschy hole-in-the-wall boutiques. There are plenty of sex stores - try Rock Hard at 518 Castro Street - so you can browse for naughty toys, too.
Pick out some fancy duds for the evening, and head back to the hotel to change for pre-theater cocktails at Martuni's, a gay piano bar slash martini joint that has perfectly prepared cocktails and a rowdy scene. Stop in at the right time and you'll be able to catch some regulars belting out show-tunes in the back room. If you're feeling brave, go ahead and join in.
From Martuni's it's just a ten-minute walk to the Yerba Buena Center for the Arts, one of the gems of San Francisco's cultural landscape. Anything from modern dance to contemporary theater is on offer here, and the venue also has a delightful urban garden for evening strolls. Try to catch a show from The Lamplighters, an alternative opera company specializing in Gilbert and Sullivan operettas.
Post-theater it's off to AsiaSF for Asian-influenced bites and a little drag cabaret. Performers strut their stuff on a catwalk bar, and though you may have to watch out for bachelorette parties, it's usually a fun, campy scene. Once you've eaten and laughed, head back to The Scarlet Huntington and relax your muscles in your room's soaking tub; tomorrow it's museums and art galleries !