Monterey To Simi Valley: Food, Wine, Jellies, and History

From Monterey Bay, head south along the coast through the wild grandeur of Big Sur to friendly San Luis Obispo, Santa Ynez Valley wine country, and Santa Barbara’s stretch of perfect coast known as “the American Riviera.”

Trip length: 4 days
Total distance: 319mi/513km


MONTEREY. See colorful jellies and watch a diver hand-feed sharks at the incomparable Monterey Bay Aquarium . For lunch, head downtown to refined Restaurant 1833 , housed in one of California’s oldest adobes. The hip twist on American staples makes the most of local ingredients—like fresh Monterey Bay salmon and just-picked vegetables from the nearby Salinas Valley. Tour adjacent historic streets—some of the oldest in the state. INFO Monterey Convention and Visitors Bureau ; 888/221-1010

PACIFIC GROVE (3mi/5km; 8min). Take a seaside stroll on Oceanview Boulevard, then enjoy exceptional hospitality at Fandango (don’t miss the short ribs slowly braised in red wine). Stretch your legs on adjacent Asilomar State Beach, a great place for whale watching. INFO Pacific Grove Chamber of Commerce ; 831/373-3304

CARMEL-BY-THE-SEA (6mi/7km; 14min). Visit Point Lobos State Reserve, a mosaic of wave-battered headlands, deep blue coves, and wildflower meadows. Dine at Cantinetta Luca , a refined yet rustic (much like Carmel itself) Italian eatery. Visit the Carmel Mission, one of the prettiest in the state. INFO Carmel Chamber of Commerce ; 831/624-2522


SAN LUIS OBISPO (146mi/235km; 2hr 22min). Follow the Coast Highway (SR 1) south through spectacular Big Sur to this pretty college town, with fun shops and shady sidewalks. For eclectic contemporary fare, try Novo , where the patio overlooks a tree-lined creek and local ingredients shine year-round. INFO San Luis Obispo Visitors and Conference Bureau ; 805/541-8000

SANTA MARIA (33mi/53km; 34min). Follow the smell of oak smoke to Shaw’s Steakhouse (714 S. Broadway St.; 805/925-5862) for traditional Santa Maria style tri-tip. For a taste of the region’s booming wine culture, reserve a table for two at the romantic Garden Room , where the wine list showcases labels from the surrounding (and celebrated) Santa Ynez Valley wine country. INFO Santa Maria Valley Chamber of Commerce ; 805/928-7559

LOS ALAMOS (20mi/32km; 25min). Stop at Bell Street Farm for sophisticated picnic fixings—think just-baked olive bread and artisanal cheeses—then head south into the Santa Barbara County wine country on bucolic State Route 154. INFO Santa Ynez Visitors Association ; 805/686-0053


SANTA BARBARA (45mi/72km; 56min). Heading south on SR 154, pause to take in sweeping views of “the American Riviera” as you descend from the peak of San Marcos Pass. Pair local wines and first-rate food at Wine Cask , one of the city’s most comprehensive wine and dine experiences. For refined Sicilian fare, try Olio e Limone . Shop along State Street, or see where the wild things are at the intimate Santa Barbara Zoo . INFO Santa Barbara Conference & Visitors Bureau and Film Commission; 805/966-9222

OXNARD (38mi/61km; 42min). Stop in at the California Welcome Center for maps and info. Don’t miss the kosher tapas at Tierra Sur , a contemporary Mediterranean-influenced restaurant inside Herzog Wine Cellars (Note: the winery and restaurant are closed on Saturdays.) INFO California Welcome Center ; 805/988-0717


MOORPARK (21mi/34km; 34min). Visit Underwood Family Farms for fresh, local produce. At Café Firenze , share a table with chef-owner Fabio Viviani, “Top Chef” Season Five fan favorite. Make arrangements early: only one Chef’s Table reservation is offered per night. INFO Moorpark Chamber of Commerce ; 805/529-0322

SIMI VALLEY (7mi/11km; 12min). Step aboard Air Force One at the Ronald Reagan Presidential Library and Museum . Stroll the grouns for views from valley to sea. Next, order a piled-high pastrami sandwich at The Hat , a Southern California classic since 1951. INFO Simi Valley Chamber of Commerce and Visitor Center ; 805/526-3900