San Francisco is a city for walking, so bring your comfortable walking shoes. There are a lot of great places just to walk down the street, check out the stores, shops, and maybe stop in a restaurant or two.
Castro Street (between Market and 20th Streets). This is the center of the original gay area of the city. (It’s now impossible to determine the center of just about any culture these days.) If this bothers you, don’t go, but it has great restaurants and shops (talk about fashion and style). We almost elected a gay mayor a while ago, so guys holding hands is no big deal anymore.
Chestnut Street (Fillmore to Gough): One of the trendier areas. Ristorante Parma is here.
Haight-Ashbury (from Haight and Masonic to Haight and Stanyan): Where “hippies” were invented, and there are still a lot of very weird shops (and even weirder residents). If you seek the strange, this is the place.
Union Square (surrounded by Post, Powell, Stockton, and Geary Streets). Fancy shops (Hermes, Wedgwood, Saks, Macy’s, Niemann-Marcus ) and great hotels on the other corners. Cable cars run down one side (“Powell Street”).Go eat at John’s Grill, the Rotunda, or, for breakfast, Sear’s. (See restaurants.)
Union Street (from Steiner to Van Ness): Sometimes called “Cow Hollow” from the dairy farms of the 1850’s, this is now the trendiest street in town. Go mingle with the ‘beautiful’ crowd at Perry’s.(see “restaurants” above.)
Pacific Heights, Pacific and Broadway between Presidio and Fillmore. (This is Steve & Debra’s neighborhood.) Who else lives here: Gordon Getty ($7 billion), next to him Larry Ellison, CEO/founder of Oracle (more billions), Meg Whitman, founder of eBay, and former CEO of HP also lost the run for Governor (look for the robot on Broadway at Broderick), John Sperling, founder of University of Phoenix ($34 million home). If Steve is in town, he’ll walk the dogs and show you around.
Presidio Terrace. Circular street off of Arguello, south of Washington. Nothing but mansions. One of the houses is Senator Diane Feinstein so, if she’s in town, there’s a guard at the gate and you’re out of luck.
Sea Cliff. Look for the entrances on Lake Street between 20th and 26th Avenues. Robin Williams lived here. His son Cody now does. Sharon Stone’s place sold for $13 mil. An unmarked trail leads to Baker Beach with spectacular views looking back at the Golden Gate Bridge.