Max Whittaker
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With its iconic bridge, historic cable cars, and beautiful Victorian architecture, San Francisco is undeniably one of the world’s great cities. The entire region, in fact, demands to be explored. The vibrant and diverse East Bay, with cities like Oakland and Berkeley, is a cultural and culinary hotbed. Napa Valley and Sonoma County produce some of the best wine in the world. San Jose, and the Silicon Valley, is an essential hub of innovation. Plus, you’ll find quaint waterfront towns, incredible shopping, fantastic museums, and endless outdoor delights at Point Reyes National Seashore.
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Santa Cruz CountySanta Cruz
The ultra-mellow beach town of Santa Cruz along Highway One has a decided split personality, and both sides are cool. First, there’s family fun at the Santa Cruz Beach Boardwalk, a yesteryear-style esplanade lined with arcade games, corn dogs, a wooden roller coaster, and a historic carousel. Then there’s downtown Santa Cruz, where college students browse for vintage and boho chic, and down-to-earth restaurants focus on healthful meals made of organic, local ingredients.
If you love nature, Santa Cruz makes an excellent launching pad. Board a boat tour from the wharf for whale-watching—grays, blues, or humpbacks, depending on the time of year—or take a winding drive in the Santa Cruz Mountains to see the ancient trees at Big Basin Redwoods State Park. And there’s another nature-inspired gem tucked in these hills: a generous selection of wineries, most specializing in Pinot Noir, Chardonnay, and Cabernet Sauvignon.
But at its heart, Santa Cruz is a surf town, dating back to 1885 when three visiting Hawaiian princes rode the local waves on redwood planks, and where today’s top surfers seek out quintessential California breaks at Steamer Lane and Pleasure Point. Need more proof? The late legendary surfer Jack O’Neill, wetsuit pioneer and elder statesman of everything surf-related, made Santa Cruz his home. The O’Neill Coldwater Classic and other international surfing contests take place here every year.
The century-old Santa Cruz Wharf is the longest wooden structure of its kind on the West Coast—a staggering 2,701 feet/823 meters long. Walk to the end to get a bird’s-eye view of Steamer Lane surfers to the north, or come at dusk to watch the lights glow on the colorfully lit Santa Cruz Beach Boardwalk. Along the waterfront, you can rent kayaks, standup paddleboards, or motorboats. Stroll past the fresh fish restaurants and souvenir shops and strike up a conversation with fishermen angling for perch, rockfish, and lingcod. Better yet, join ’em. You don’t need a license to fish from the pier, and local tackle shops can get you outfitted.
Santa Clara CountySilicon Valley
Welcome to California’s tech-centric brain pool. Stretching roughly from the city of Belmont down to San Jose around the south end of San Francisco Bay, Silicon Valley is home to some of the largest technology corporations in the world. The area is marked by sprawling campuses, including that of Stanford University and Fortune 500 companies like Google, Apple, and Facebook. Hike or bike a trail and overhear the next big idea. Visit a museum that blinks and buzzes with what-if innovations. And enjoy the riches of a booming economy, with performance spaces, high-end shopping, and multi-starred restaurants.
See where the magic happens by exploring Silicon Valley’s tech hubs. At the Googleplex in Mountain View, you can witness “Googlers” talking, texting, and riding the signature yellow bikes. Only an official badge can get you into the gourmet-food-for-free cafeterias—but anyone can visit the Android sculpture garden with pieces commemorating the release of different operating systems. Just south in Cupertino, pick up logo t-shirts, caps, and mugs at the Apple Park Visitor Center. North in Menlo Park, you’ll find the Facebook campus’s iconic “like” sign in baby blue—a popular selfie backdrop. Don’t miss the modest building in Palo Alto where it all began: the garage at 367 Addison Avenue where, in 1939, Bill Hewlett and Dave Packard forged a partnership that would become HP.
San Francisco CountySan Francisco
It may measure less than 50 square miles and have a population that doesn’t even crack a million, but San Francisco justly ranks as one of the greatest cities in the world. Famous for grand-dame Victorians, cable cars, a dynamic waterfront, and a soaring golden bridge, this city truly has it all. With trend-defining cuisine ranging from Michelin-starred dining to outrageous food trucks; world-renowned symphony, ballet, theater, and opera; plus almost boundless outdoor adventures, San Francisco justifiably stands out as one of the ultimate must-visit cities on any traveler’s wish list.
The hardest part may be deciding where to go first. (Well, that and packing for the city’s famously unpredictable weather.) The Golden Gate Bridge is one of the city’s most iconic landmarks; you can walk or bike across the span to the Marin Headlands. Or stay on the San Francisco side and stroll over to the San Francisco Palace of Fine Arts, the Presidio, or Lands End, a rugged, windswept playground where you can watch for whales and check out the ruins of the Sutro Baths.
Fisherman’s Wharf beckons with its seafaring vibe and amazing seafood restaurants; look out across the water and you’ll see another fascinating destination not to be missed, Alcatraz Island. The bustling plazas of Union Square and Ghirardelli Square offer shopping and more great dining options. The city’s patchwork of distinct neighborhoods—the Mission District, Chinatown, North Beach, Haight-Ashbury, Nob Hill, and so many more—offer endless diversions both day and night.
Despite its famously steep hills, San Francisco is remarkably easy to get around. Clanging cable cars are beloved icons and a convenient way to travel between the waterfront and Union Square. Historic streetcars run along the Embarcadero with stops for Fisherman’s Wharf, the Ferry Building Marketplace, and Oracle Park, home of the Major League’s Giants baseball team. For an easy, affordable ride, look for one of hundreds of bikeshare stations and hop on a Bay Wheels bike (or ebike) and go.
The underground BART metro system travels within and beyond San Francisco, with routes south to San Francisco International Airport and east to Berkeley, Oakland, Pleasanton, and other communities. And San Francisco’s local MUNI buses travel citywide.
Insider tips: If you plan on visiting several of the attractions it can cover, consider getting a CityPASS; it allows prepaid admission to the California Academy of Sciences; a Blue & Gold Fleet Bay Cruise Adventure; a choice between the Aquarium of the Bay or the Walt Disney Family Museum; and a choice between The Exploratorium or San Francisco Zoo and Gardens.
Another economical option is the San Francisco C3; with it, you can visit any three attractions, choosing from the above CityPASS options plus SFMOMA, Bay City Bike and Parkwide Bike Rentals, and the de Young Museum + Legion of Honor.
Sonoma CountySanta Rosa
With nearly 180,000 residents, this is Sonoma County’s largest commerce hub, but even so, Santa Rosa still feels pretty cozy. Its small-town heart prides itself on a rich agricultural heritage, burgeoning arts and brewpub scene, and two famous native—a horticulturalist and a cartoonist.
Experience the city’s casual-warm vibe at the welcoming Railroad Square Historic District. Once the home of bootleggers and ladies of ill repute, the square now hosts 40-plus shops and eateries clustered around the restored 1903 Northwestern Pacific Railroad train depot. Every day the SMART train heads south to Marin County, but there are plenty of reasons to stay right here. Wander the square and admire Santa Rosa’s early 20th-century brick buildings. Order a demitasse of Espresso No. 9 at Flying Goat Coffee. Pop in for breakfast at Omelette Express. Browse through vintage dresses, hats, and period costumes at Hot Couture, or marvel at delicate china teacups perfect for pinky-lifting at Whistlestop Antiques. Have dinner or spend the night at the stately Hotel La Rose, built by Italian stonemasons in 1907.
Santa Rosa’s under-the-radar SOFA arts district (South A Street) is a fashionable home for creative types. The Santa Rosa Arts Center and neighboring art studios sponsor events, classes, and concerts. Entrepreneur and chef Liza Hinman has transformed an aging building into the ultra-hip, mid-century-modern Astro Motel, a sister endeavor to her Spinster Sisters restaurant, where nightly specials include eggplant croquettes, roasted bone marrow, and Moroccan-style carrots. A few footsteps away, the Luther Burbank Home and Gardens honors the self-taught horticulturist Burbank, who took advantage of Sonoma County’s rich soil to develop the Shasta daisy and Santa Rosa plum. Take a home or garden tour and visit the Carriage House Museum at this registered National and State Historic Landmark.
All around town, you’ll notice larger-than-life statues of Snoopy, often accompanied by Charlie Brown, Woodstock, and Lucy. Cartoonist Charles Schulz lived and worked in Santa Rosa from 1969 until his death in 2000, claiming Sonoma County as an inspiration for his iconic Peanuts comic strip. At the Charles M. Schulz Museum, visit a re-creation of the artist’s studio to see his sketches, then head next door to Snoopy’s Home ice rink for year-round skating.
Santa Rosa’s brewpub culture thrives at Plow Brewing Company, Third Street Aleworks, and Russian River Brewing Company, where innovative brewing methods are creating some of California’s most coveted beers, like the triple IPA Pliny the Younger. And you can’t forget you’re in wine country—tasting rooms are located right in the city’s heart. Santa Rosa Vintners Square makes sipping-and-sampling neighbors out of D’Argenzio Winery, Topping Legnon Winery, and Fogbelt Brewing Company—all dotted around a lovely terrazzo-like outdoor setting.
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