Circle The Bay For Fresh Flavors, Charming Towns, And A Peek At Mavericks

Sample the flavors found in one of the world’s culinary capitals—San Francisco—plus wine country, waterfront, and a chance to see the state’s biggest, baddest surf break.

Trip length: 4 days
Total distance: 207mi/333km

DAY 1
SAN FRANCISCO. Visit the California Welcome Center at PIER 39 for insider tips on this city’s coolest corners. Dig into cornmeal-crusted oysters at Burritt Tavern in the revamped Mystic Hotel, then amble over to Jamber , where all the wine is on tap. INFO California Welcome Center ; 415/981-1280

OAKLAND (12mi/19km; 20min). Cross the Bay Bridge to Bocanova , in Jack London Square, for Pan-American fare (think short rib empanadas and a quinoa salad with duck confit) overlooking the yacht harbor and the Oakland estuary. Visit the extraordinary Oakland Museum of California for outstanding natural history and art. INFO Oakland Convention and Visitors Bureau ; 510/839-9000

BERKELEY (8mi/13km; 15min). Sample house-made charcuterie at http://www.revivalbarandkitchen.com/" onclick="tracking.run('Partner_Referral','revivalbarandkitchen.com/')">Revival Bar + Kitchen ; the eatery’s “whole-hog” butchery program works closely with local ranchers. For more refined dining, try the French fare at Michelin-recommended Bistro Liaison . Stroll the Berkeley campus and nearby Telegraph Avenue to feel like a college kid again. INFO Berkeley Convention and Visitors Bureau ; 510/549-7040

DAY 2
DANVILLE (22mi/35km; 3min). Start with a hike in Mount Diablo State Park . From the South Gate Entrance Station it’s a short trip to Rock City, an outcropping of unusually large sandstone formations. Atop the summit, views stretch beyond the Golden Gate to the Farallon Islands. INFO Mount Diablo State Park ; 925/837-2525

NAPA (50mi/80km; 50min). Wash down wood-grilled steaks and chops with top-shelf local reds at Mustards Grill . Prefer white wine? Try Fish Story for sustainable seafood and farm-fresh produce on the Napa Riverfront. The inviting downtown offers street art, galleries, and tasting rooms. INFO Visit Napa Valley ; 707/260-0107

DAY 3
SAN RAFAEL (35mi/56km; 46min). Dig into wood-fired pizzas with organic, seasonal toppings at Terrapin Crossroads . You just might catch a jam session featuring proprietor Phil Lesh, former bass player of the iconic Bay Area band The Grateful Dead. Catch an art flick at the meticulously restored Christopher B. Smith Rafael Film Center, where stars like Sean Penn and Keira Knightly often stop by to talk about their latest films. INFO Marin Convention and Visitors Bureau ; 415/925-2060

SAN FRANCISCO (18mi/30km; 35min). Join the throngs at the Ferry Building Marketplace. Sample first-rate cheeses at Cowgirl Creamery , artisanal loaves at Acme Bread Company , and handmade chocolates at Recchiuti Confections. Work off your meal with a leg-stretcher along the Embarcadero to AT&T Park, home of the World Series champs, the San Francisco Giants (behind-the-scenes ballpark tours offered daily). INFO San Francisco Travel Association ; 415/391-2000

DAY 4
SAN MATEO (20mi/32km; 25min). Visit the California Welcome Center  for local favorites, like nearby Filoli, a once-private country estate now open to the public. For contemporary takes on traditional Asian dishes, try Attic . Think Korean barbecue lettuce wraps and Filipino street-food-inspired adobo wing “lollipops” (chicken wings with an adobo glaze). INFO California Welcome Center ; 650/578-8033

PALO ALTO (16mi/26km; 19min). Take a podcast-guided tour of Stanford University, Silicon Valley’s incubator of innovation. Be sure to visit the glorious Rodin sculpture garden. Then kick back at Coconuts Caribbean , where chicken is smoked slowly over allspice wood and brushed with a tangy jerk sauce. INFO Palo Alto Chamber of Commerce ; 650/324-3121

HALF MOON BAY (26mi/42km; 35min). Drive through coastal hills to this cozy oceanfront village. Dine al fresco (there are plenty of heat lamps) at Sam’s Chowder House . If an oyster stew with bacon and cream sounds heavy, consider the cold-water leviathans breaking at “Mavericks,” surfing’s most notorious monster wave, visible from the safety of the heated patio. INFO Half Moon Bay Coastside Chamber of Commerce and Visitors Bureau; 650/726-8380