1. Where to Stay
Lounge on your waterfront balcony—or in front of your in-room fireplace, on cooler nights—at the Waterfront Hotel (from $109), a chic boutique outpost just renovated in 2008. The spot is in Jack London Square, where you can browse the artisan market (Saturdays and Sundays, 10 to 4) and farmers’ market (Sundays, 9 to 2).
Escape the rush at the Hills Bed and Breakfast (from $130), a secluded, one-suite guesthouse in the woodsy Oakland Hills area. Complimentary breakfast fare includes granola from Alice Waters’s Café Fanny and apples and tomatoes fresh from the on-site garden. Snag a seat on the outdoor deck for San Francisco Bay views.
Finagle your way into the Bellevue Club (from $109), a private social club set in a 1929 Beaux Arts building. This unpublicized jewel rents rooms to non-members on a case-by-case basis. (Hint: They’re usually accommodating if you mention that you’re visiting family in Oakland.) The on-site restaurant plans its rotating weekend dinner menu around whatever’s freshest at the nearby Grand Lake Farmers Market.
2. Where to Eat
Book a table at least a week in advance at Commis, a minimalist, 31-stool eatery where former El Bulli apprentice James Syhabout earned Oakland’s first ever Michelin star in the 2010 guide. All seats offer views of the open kitchen, where you can watch Syhabout’s team create Northern California favorites like roasted Sonoma County duck and Mendocino porcinis matched with foraged produce like wild elderberries and pears.
Fill up on Southern-style cuisine at Picán, where local produce like green tomatoes and sweet corn is served at its seasonal peak. Call a few hours ahead to reserve a portion of the signature buttermilk fried chicken, which undergoes a three-day brining process and tends to sell out before close.
Sample Pebble Beach oysters and Pacific mahimahi at Lake Chalet, a 100-year-old boathouse transformed into a seafood destination in August 2009. The no-reservations outdoor deck fills up quickly; admire the same view without the wait by reserving a Lake Merritt–facing table in the second-floor dining room.
Gorge on California-tinged Latin dishes at Bocanova, where chef Rick Hackett—also of the San Francisco Ferry Building’s MarketBar—embellishes shareable seasonal specialties like Yucatán seafood stew with local grapefruits and tomatoes.
3. What to Do
Explore Oakland’s wineries by bike on the East Bay Winery Bike Tours (Fridays, Saturdays, and Sundays, 11:30 a.m.), a group trip that takes cyclists to three to four of over a dozen small wineries that have opened throughout Oakland in the past five years. The $89 cost covers tasting fees and free transportation for any bottles or cases you buy.
Sample soon-to-be-released single-origin coffees for free at Blue Bottle’s headquarters (Saturdays at noon), which opened in this twenties-era warehouse last year. Pair your brew with treats like vanilla-saffron snickerdoodles and absinthe-sesame biscotti.
Skip Art Murmur’s boozy First Fridays event—it now draws such large crowds that you can barely see the art. Instead, create your own art crawl among eleven of the area’s galleries, which host Saturday open houses. Start at Vessel, where sculptures, paintings, and handmade jewelry are showcased in a turn-of-the-century horse stable, and end at Flora, a flower depot turned cocktail bar that serves up unusual drinks like the Steps of the Empire: tequila, local citrus juices, and coffee-cinnamon-chipotle syrup.
Mingle with area hipsters at the Fox Theater, a lavish twenties movie palace that now hosts bands like Widespread Panic (October 15-17) and Florence and the Machine (November 5). Just don’t expect PBR: The Den lounge next door offers elderflower and Tuaca-infused cocktails, Pointe Reyes cheeses, and charcuterie from Berkeley’s Star Meats.
4. Insider’s Tip
While Oakland’s new restaurant scene can be pricey, high-end Italian spot Adesso offers the best happy-hour deal in the city. Order wine, beer, or a cocktail—the black lager from Oakland’s Linden Street Brewery is a popular pick ($5)—and gorge on the free, unlimited smorgasbord of housemade salumi, locally sourced cheeses, deep-fried croquettes, and fresh pasta. It happens twice a day, from 5 p.m. to 6 p.m. Monday to Saturday, then again from 10:30 p.m. to 11:30 p.m. Monday through Wednesday and 11 p.m. to midnight Thursday to Saturday.
5. Oddball Day
After soaking up the emerging urban scene, seek out some California countryside within city limits. Start your day with a single-origin brew from Remedy Coffee, then wander a few blocks down and pack a picnic lunch of buttermilk-fried chicken sandwiches and strawberry shortcake at Bakesale Betty, helmed by former Chez Panisse pastry chef Alison Barakat. Grab your bike (Bay Area Bikes; from $25/day) or car and head ten miles north of downtown to Redwood Regional Park, a little-known enclave that affords views of the majestic 150-foot-tall trees without the tourist hordes you’d find in Marin County across the bay. Choose from dozens of woodsy trails—the four-mile Ridge Trail offers some of the best views of the canyon along the base of the park and includes multiple areas to stop for lunch. On your way back to downtown Oakland, stop at the Smithsonian-affiliated Chabot Space & Science Center, where the Friday- and Saturday-night Dinner, Movie, and the Universe deal offers a four-course meal, a screening in the digital planetarium, and access to the three giant telescopes in the observatory ($32.95; 6 and 8 p.m.).
The Oakbook’s weekend guide offers news on arts and culture happenings around the city.
The East Bay Express’s food page is the go-to source for Oakland restaurant openings.
Get the latest on the local music scene from the 38th Notes blog.
Find out when the next bus or subway is coming without leaving your bar stool, via 511.org’s real-time, GPS-aided transit updates.