Union Square is the commercial hub of San Francisco. Most major hotels and department stores are crammed into the area surrounding the actual square, which was named for a series of violent pro-union mass demonstrations staged here on the eve of the Civil War. A plethora of upscale boutiques, restaurants, and galleries occupy the spaces tucked between the larger buildings. A few blocks west is the Tenderloin neighborhood, a patch of poverty and blight where you should keep your wits about you. The Theater District is 3 blocks west of Union Square.

If you want to meet a living San Francisco historical monument, head to the Sir Francis Drake hotel. Tom Sweeny, the head doorman dressed in traditional Beefeater’s attire (you can’t miss those $1,400 duds), has been the subject of countless snapshots -- an average 200 per day for the past 25 years -- and has shaken hands with every president since Jerry Ford.

If getting immersed into the San Francisco nightlife is on your to-do list, check out downtown’s most glamorous and colossal nightspot. Ruby Skye (www.rubyskye.com) led a previous life as an 1890s Victorian playhouse, and many of the beautiful Art Nouveau trimmings are still in place. Mission District clubbers won’t go near the place -- way too disco -- but for most it’s a safe bet for a dance-filled night in the city. Be sure to call or check the website to make sure there isn’t a private event taking place.