Huckleberry Botanic Regional Preserve

If you skipped the snacks on your flight, try your luck at Wood Tavern (6317 College Ave between Alcatraz Ave and 63rd Ave, 510-654-6607), a New American gastropub that’s as tough a reservation as anything in Alice Waters’s Gourmet Ghetto. “Locally sourced” may be a mantra you’ve heard all too often, but in California it takes on a totally different meaning: Regional specialties include fennel-and-lavender-flavored Purple Haze chèvre on the cheese plate, and fresh-picked asparagus with truffle oil and Parmesan. A more low-key option is Pizzaiolo (5008 Telegraph Ave between 50th and 51st Sts, 510-652-4888), where a wood-burning oven fires excellent pizzas like the wild nettle and pecorino, or the pizze al dia—whose ingredients change night to night, depending on the whims of the chef.

The city lights across the bay might beckon, but Oakland outshines SF in at least one nightlife arena: the dive bar. Neon signage and a resident boxer mark the eccentric George Kaye’s (4044 Broadway between 40th and 41st Sts, no phone), where the beer is cheap, showcased artists are local, and the space is tight enough for you to strike up a conversation with the pioneering young resident you might want to house-swap with on your next trip. Heading further downtown, the Ruby Room (132 14th St between Oak St and Madison St, 510-444-7224), with its haze of red lighting and cigarette smoke, positions itself at the epicenter of Oakland cool. Its soundtrack includes everything from punk to honky-tonk, and the crowd even ventures in from San Francisco, nostalgic for the vibe of a pregentrified Mission District.If you’ve got only a couple of days in the city, damage control is key. Follow the Ruby Room’s last call with a trip to the Tacos Mi Rancho truck (14th St at First Ave) a few blocks east, and hop on line for greasy avocado tortas and authentic Mexican tacos al pastor with pork shaved fresh from the rotisserie spit.

The East Bay’s finest asset, of course, is its weather (often ranked as the nation’s best), and the string of ridgeline parks that runs along Oakland’s eastern edge lets you take full advantage. (Folks without a car can ride the BART train [bart.gov] to most of the city’s natural sights, but it’s still a good idea to rent a vehicle.) Start your trek with a two-mile trail cutting through manzanita and chamise groves in Huckleberry Botanic Regional Preserve (Skyline Blvd between Broadway Terr and Snake Rd, 510-644-0436). If you head back downtown, don’t miss the bustling Lake Merritt, an Oakland centerpiece ringed by grassy parks and a 3.5-mile walking path. Then stop in to refuel at Merritt Restaurant & Bakery (203 E 18th St at Second Ave, 510-444-6955), a chicken-and-waffle institution with diner-style seating, fridges stocked with tall frosted cakes and a family-friendliness that draws from all swatches of Oakland’s social fabric.

Finally, venture into Old Oakland for a peek at the city’s DIY creative enterprises in action. Decor shop FiveTen Studio’s loftlifke gallery (831 Broadway between 8th and 9th Sts, 510-451-9900) houses cutting-edge, limited-edition furnishings, like a redwood-and-steel coffee table by the architect–co-owner, and glass-blown globular lamps that also hang in SF’s de Young Museum. You can’t sneak much of FiveTen’s pieces back on the plane, but the boutique—anchoring an up-and-coming Victorian row of shops—probably best captures Oakland’s on-the-cusp mood.

THE TAB

Two nights, two people

Flight $610
Car rental $80
Hotel $418
Meals $320

TOTAL $1,428

Travel: JetBlue offers nonstop service to Oakland from JFK, but you might find a cheaper fare if you fly a major airline like American to San Francisco International Airport and take the BART train to Rockridge.

Travel time 5hrs 30mins