In Alamo Square Park (Hayes St at Steiner St), you’ll be rewarded with some of the best views of downtown. From there, it’s a five-minute walk to Hayes Valley, whose independent boutiques and art galleries might remind you of Wicker Park. If you have serious cash to drop, Nida (544 Hayes St between Laguna and Octavia Sts, 415-552-4671) is a must-visit, offering men’s and women’s clothing from designers such as Vanessa Bruno and Neil Barrett. And check out the sale racks at Azalea (411 Hayes St at Gough St, 415-861-9888)—there’s almost always a deal from A.P.C. or Loomstate—before going to the back of the shop for a quick manicure.

Don’t bother renting a car. San Francisco’s transit (sfmuni.com) is cheap ($18 for a three-day pass) and efficient, and a ride on one of San Francisco’s vintage streetcars (pictured) transports you in style to the downtown shopping area, Union Square (Powell St at Geary St). Be aware that the nearby Tenderloin neighborhood is hypersketchy—we’re talking crack smoking in broad daylight—but it’s also home to the best breakfast place in town: Dottie’s True Blue Cafe (522 Jones St at O’Farrell St, 415-885-2767).

You could easily spend a day exploring the largest Chinatown outside of Asia. Lovers of Italian food and Beat culture should head to the adjoining North Beach neighborhood (sfnorthbeach.org). Avoid the tourist traps along Columbus Ave and walk uphill to Trattoria Contadina (1800 Mason St at Union St, 415-982-5728) for great gnocchi served with a view of the cable-car line. Bibliophiles should check out legendary Beat hangout City Lights Bookstore (261 Columbus Ave, 415-362-8193, citylights.com).

If history is your thing, you can’t go wrong with a free guided walking tour (sfcityguides.org). Or head out to Alcatraz ($24.50/ticket, alcatrazcruises.com) for an excellent audio tour narrated by former guards and prisoners. San Francisco’s more recent history as the epicenter of the hippie movement is well-documented at the intersection of Haight-Ashbury, but you’re more likely to encounter panhandling punk kids than flower children these days.

For an urban escape, nearby Golden Gate Park has plenty of activities as it stretches all the way to the Pacific. Sip matcha at the Japanese Tea Garden, walk the Redwood Trail at the San Francisco Botanical Garden (sfbotanicalgarden.org), or just watch bongo-playing potheads do their thing. Filled with lots of homey restaurants and cute shops, the Inner Sunset neighborhood hugs the south-central boundary of the park. Or head north of the park to the Inner Richmond district for cheap pan-Asian eats. The outstanding tea-leaf salad is a must-try dish at Burma Superstar (309 Clement St at 4th Ave), and while you’re waiting for your table—you won’t mind waiting for food this good—drop into Park Life, a cool art gallery-cum-design shop (220 Clement St at 3rd Ave, 415-386-7275).

On warm days, make like Jimmy Stewart in Vertigo and explore the garden at Mission Dolores (3371 16th St at Dolores St) before grabbing a salted caramel ice cream cone at Bi-Rite Creamery (3692 18th St at Dolores St, 415-626-5600) in the Mission District. Along nearby Valencia and Guerrero streets, boutiques cater to an indie clientele; stop by Minnie Wilde (3266 21st St at Valencia St, 415-642-WILD) for vintage-inspired dresses before ordering an out-of-this-world deep-dish pie at Little Star Pizza (400 Valencia St at 15th St, 415-551-7827). One taste and you may almost forget that Chicago invented the stuff. (No offense to hometown faves Pizzeria Uno and Giodano’s.)

THE TAB

Two nights, two people
Airfare $500*
+ Hotel $518
+ Meals $170
TOTAL $1,188

Travel time 4 hours

For more information, visit onlyinsanfrancisco.com

*Southwest and American both fly direct; with a little advance planning, you can snag round-trip tickets to nearby Oakland or SFO for $250 or less.