San Francisco Bay Loop sanfranciscobayloop

Trip 3-5 days 10 stops

San Francisco Bay Loop

This loop drive takes in the best of the Bay Area, a diverse, dynamic, and beautiful region with lively cities, celebrated wine country, and outstanding natural wonders. Start at the gateway to San Francisco, one of the world’s most beautiful cities, to head north across the Golden Gate Bridge. Explore coastal parklands before heading northeast to Napa and Sonoma wine countries. Continue circling the bay to visit Six Flags Discovery Kingdom, with rides and exotic animals, then onto the East Bay city of Oakland, a hot bed of outstanding restaurants. Drive south to San Jose and the tech-y Silicon Valley, home to Google and Apple, then head to the coast for more family-friendly fun in Santa Cruz. Finish in San Francisco for shopping, dining, nightlife, and other urban attractions. 

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Golden Gate Bridge

Golden Gate Bridge
See one of the world’s most famous landmarks, spanning an elegant bay

Start your trip with a visit to one of the most iconic spans in the world. With towers soaring 746 feet/227 meters into the sky, its span arcing across the mouth of San Francisco Bay, and all of it painted fire-engine red, the Golden Gate Bridge makes a dramatic destination, and a great way to begin a tour of the region.

If you’re scratching your head as to why a bridge called “Golden Gate” is in fact red, here’s why. It’s generally accepted that the mouth of San Francisco Bay—the narrow strait that the bridge spans, was named Chrysopylae (Greek for “Golden Gate”) by early explorer John C. Fremont. (Captain Fremont thought the strait looked like a strait in Istanbul named Chrysoceras, or “Golden Horn.”) So it makes sense that the bridge is named after the expanse of water that it crosses. But what about that crimson color? Call it an unexpected surprise. When the steel for the bridge was first installed in place, it was only covered with red primer. A consulting engineer liked it, suggested the color be kept, and helped develop the bridge’s final paint color.

While you can simply drive north across the bridge, it’s more fun to walk (even if it’s just for a portion of the span). Note that it can be a bit nippy and windy on the span, especially when the fog slips in (common in summer), so dress in layers, and bring a hat or flip up a hood to keep your head warm. Riding bikes across the bridge is another fun option—rental companies abound (two favorites are Blazing Saddles and San Francisco Bicycle Rentals); most bikes come equipped with detailed route maps showing you where to ride from San Francisco across the bridge to idyllic towns, such as Sausalito and Tiburon, in neighboring Marin County. (For extra fun, catch a local ferry to get back to the city.) Back on the bridge, there’s a nice gift shop and a café at the south (city) end, and paths let you wind down to historic Fort Point, completed in 1861 as a military outpost to protect the gate before there was a bridge. Look up for a remarkable view of the bridge’s underbelly, a spectacular network of massive girders, enormous columns, and impressive cables.

Now it’s time to climb in the car and head north to Marin County and the closest grove of coast redwoods at Muir Woods National Monument.

Next Stop
Muir Woods National Monument (11mi/18km; 21min)
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Muir Woods National Monument

Muir Woods National Monument
Cross the Golden Gate Bridge to the land of the giants

Heading north into Marin County, you’ll get sweeping views of this lovely region, known for desirable towns tucked into lush canyons and dotting the bayfront and rugged coastal hills. The region is also notable for extensive parkland (80 percent of the county is set aside as park or open space), and one of its premier parks is Muir Woods National Monument protects the last stand of uncut old-growth coast redwoods in the Bay Area, where loggers had all but denuded the region by the late 1800s.

Originally established as a national monument in 1908 by President Theodore Roosevelt, it was named in honor of the revered naturalist John Muir, who declared the site was “the best tree-lover’s monument that could possibly be found in all the forests of the world.” Even on busy days in summer, there is a remarkable hush here, especially if you arrive in early morning. Follow raised boardwalks, built to protect the redwoods’ sensitive root structure, to see the arrow-straight redwoods, some over a century old, soaring 250 feet/76 meters overhead. For an unforgettable experience, check the park’s activities calendar to go on a guided walk at dusk.

“the best tree-lover’s monument that could possibly be found in all the forests of the world.” 

Keep in mind that the road to the park is twisty and narrow, and parking lots often fill up early in summer and on weekends. (Miss a spot in the lots and it can be a long, long walk to your car.) Your best bet is to take the public Muir Woods shuttle (March through October) from nearby Sausalito, or book a tour with a local shuttle service or tour operator.

From Muir Woods, take winding Highway One north to another exceptional, uncrowded park, Point Reyes National Seashore.

Next Stop
Point Reyes National Seashore (23mi/37km; 46min)
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Anita Ritenour/Flickr

Point Reyes National Seashore

Point Reyes National Seashore
So far out you seem to be in the sea

Follow the coast, past broad Stinson Beach and the sparkling Bolinas Lagoon (a great place for kayaking and birding) to this extraordinary peninsula. Jutting dozens of miles out into the sea, Point Reyes is loaded with amazing discoveries, including remarkable wildlife, deep forests, dramatic sea cliffs, and remote beaches.

No matter what time of year you visit, there’s something extraordinary to see and do. In winter, travel to the tip of the point (a shuttle takes you the last few miles) to look for migrating gray whales passing remarkably close. (It helps when you just out into their swimming lanes). In spring, walk the trail to Chimney Rock to see countless wildflowers (look for puffins nesting on oceanfront cliffs), or follow a trail lined with irises into a rare Bishop pine forest. In summer, watch the cool fog tumble in, then have a cup of cocoa in the cozy village of Point Reyes Station. And in fall, listen for the eerie bugle of tule elk bulls; can usually spot individuals or small herds of these native elk in the Tomales Point preserve area, at the tip of the park.

To get yourself oriented, stop by the outstanding Bear Valley Nature Center, with kid-friendly displays, maps, and helpful rangers. The fairly flat, stroller-friendly Bear Valley Trail makes a popular leg-stretch or bike ride.

Your road trip now heads inland to explore some of the finest wine country in the world.


Next Stop
Napa/Sonoma (47mi/76km; 1hr9min)
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Napa & Sonoma

Napa & Sonoma
Ultimate wine country luxury

Turning east you leave the drama and wildness of the coast to explore these two premier wine regions, with rolling hills and flat valleys planted with some of the most coveted grapes in the world. There are literally hundreds of wineries and tasting rooms here—in settings ranging from castles to renovated barns—with tours, special events, and wine release parties filling the calendar year-round.

Sonoma is the more western region, and tends to have more intimate feel, especially as you head further north towards the redwood forests and rugged terrain around the Russian River. A great place to get oriented is the gemlike town of Healdsburg, a place that has transformed itself from a rough-around-the-edges country town to a first-class destination. First, there’s a perfect town square, surrounded by tasting rooms filled with beautiful people, boutiques with tempting offerings at every turn, and swanky restaurants glowing at dusk. Locally grown produce gets the spotlight here, and the twice-weekly (June through October) farmers market is a model of fresh, local, and sustainably grown fruits and vegetables. Stop in at Healdsburg Shed, an expertly curated haven of kitchenware, cookbooks, and garden tools. Pick up artisanal cheeses and a fresh crusty loaf at tempting Oakville Grocery and have an impromptu nosh in the square. Finish the day with a decadent meal of pork-belly biscuits, Hamachi crudo, and squid-ink pasta at Chalkboard.

If you like twisty country roads, you’ll love the Oakville Grade, which squiggles and hairpins over the Mayacamas Range between Sonoma and Napa Valley. Here, you’ll descend into some of the world’s most celebrated vineyards, a land of grand estates, expansive tasting rooms, quaint towns, and elegant lodgings, many lining the celebrated Silverado Trail.

Here’s the best of the best, a country road trimmed with shady oaks and world-class wines, with so many wineries you could travel it for a week straight and still not visit them all. The first permanent road linking the town of Napa to Calistoga, roughly 30 miles/48 kilometers south, the Silverado Trail is the country-road counterpart to busier Highway 29, which roughly parallels the route. Drive—or better yet rent a bike and pedal—along this tranquil, scenic route, snugged up against the valley’s eastern hills.

The biggest challenge is figuring out where to stop first. Prestigious wineries with Silverado Trail addresses include Joseph Phelps, ZD Wines, and Miner Family Winery, just three of the dozens of wonderful places to sample Napa Valley’s infamous Cabernet Sauvignon and other big-bodied reds. Elegant inns include Auberge du Soleil and Solage Calistoga. To see one of the prettiest places in the whole region, take the long, leafy drive onto the manicured grounds of Meadowood Napa Valley for an al fresco lunch at The Grill, or, if you’re feeling extra splurge-y, dinner at the three-Michelin-starred The Restaurant at Meadowood.

From Napa, continue south around the eastern side of San Francisco Bay to a bayfront amusement park.

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Courtesy of Six Flags Discovery Kingdom

Six Flags Discovery Kingdom

Six Flags Discovery Kingdom
Flip out on mega coasters and see exotic animals

There’s no hiding what’s the big draw at this popular attraction in the East Bay city of Vallejo. Even before you park your car you’ll see the giant loop-de-loops, spirals, and white-knuckle descents of the park’s trademark coasters and thrill rides, such as Superman Ultimate Flight and Tsunami Soaker. Get your fill of these adrenaline pumpers, then retreat to the calming beauty of the Butterfly Habitat. Once your blood pressure is back to normal, watch entertaining dolphin and sea lion shows, see African lions and Bengal and Siberian tigers and mountain lions in naturalized enclosures, ride an elephant, or feed a giraffe.

For tamer entertainment for the little ones, let them romp around Acme Fun Factory, a two-story playhouse. There’s also a water play area just for smaller kids, plus tot-friendly rides and activities. For you, consider deluxe experiences, like finding out what Flipper really feels like on a special dolphin interaction.

Next up is a trip to hip Oakland for great food, shopping, and art.

Next Stop
Oakland (28mi/45km; 35min)
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Edgy, artsy, diverse

Drive south from Vallejo into the hilly East Bay, past the university town of Berkeley to San Francisco’s sister city. Oakland is often referred to as “San Francisco’s Brooklyn,” with the same kind of historic twists, beautiful views, and exploding food and wine scene as that New York borough. Diverse, dynamic, artsy, edgy—Oakland has seen an influx of young locals, drawn not only by the vibe but by the city’s lower rents too, have moved into downtown lofts and condos, and so have come the single-pour coffee bars, cafes, galleries, and clubs, too. Lower costs in the East Bay have also lured chefs—both established big names and new-gen kitchen whiz kids—to open restaurants here, in settings ranging from splashy Art Deco (Flora) to sleek hipster chic (Plum). 

Jack London Square, an inviting complex perched on the edge of San Francisco Bay, mixes outdoor fun with indoor diversions. The square is named after the intrepid adventurer and author of Call of the Wild and The Sea Wolf, a book allegedly inspired by tall tales told by the crusty folk who frequented the legendary—and still open—Heinhold’s First and Last Chance Saloon. Near the sloped entrance to the historic watering hole, the wall hands on the wall clock haven’t budged since April 18, 1906—the moment a massive quake struck the Bay Area, and jolted the building so much the timepiece stopped ticking. Time may have stopped, but not service, and stepping down into this little wooden shack is about as time-warpy as you can get: 19th-century gas lamps glow each evening, World War II photos photographs and memorabilia, and a small photo of a young London sitting at one of the saloon’s tables adorn the walls. Settle in and talk to your elbow-mate at the bar; you never know what tall tales you might here.

But save your visit to this historic bar until later in the day. When the sun’s up and shining, paddle a kayak around the adjacent Oakland Estuary, especially lively during the fall bird migration. Post paddle, stroll the square to visit shops, or tour two historic vessels: the Lightship Relief, a floating lighthouse which aided navigation along various U.S. coastlines from 1951 to 1974, and the USS Potomac, President Franklin Delano Roosevelt’s historic yacht (ask about bay cruises). Dine at inviting options like Baia for organic pasta, or have crab cake benedict for brunch at Oakland Grill. Farmers’ markets and outdoor movies add to Jack London Square’s neighborhood-y appeal.

From Oakland, follow the edge of the bay to California’s third largest city.

Next Stop
San Jose (41mi/66km; 46min)
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Courtesy of San Jose International Airport

San Jose

San Jose
Tech savvy, international flair

Never has this metropolis, California’s third largest city, sparkled more. The center of the booming, tech-centric Silicon Valley, San José is packed with worthy destinations, like ultra-hands-on The Tech Museum, and light and airy San Jose Museum of Art. De Anza Hotel is an Art Deco gem, while the SAP Center, which draws headline entertainers and is home to the San Jose Sharks NHL franchise, is a glassy modern palace.

And of course, there was life before silicon chips. Learn about San José’s rich agricultural and impressive ethnic roots at the expansive campus of History San José, on the southeast side of town.

So much of the magic of the modern era happens invisibly and at nano scale, but The Tech Museum of Innovation—or simply “The Tech”—in downtown San José does a great job of creating a fun laboratory and learning experience for curious people of all ages. Dive into interactive exhibits showing the power of technologies ranging from robots to gene-splicing to alternative energy. Let virtual butterflies alight on your arm, and let the kids play with the ultimate video games—you’ll probably want to play too. Another highlight is the Silicon Valley Innovation Gallery, showcasing the machines that revolutionize human thought, creativity, and communication. Man does not live by bits and bytes alone—so relax in the café, the peruse tech-and-science-y items in the gift shop (especially great for holidays and birthdays). 

For the city’s most luxurious shopping experience, visit Santana Row, a snazzy outdoor mall, a mix between California’s relaxed stylishness and a swanky European village on market day. It’s the kind of place where you can easily while away the hours, sitting on a bench perusing your purchases while nibbling fresh croissants from Cocola. And, in the ultimate Silicon Valley indulgence, why not custom-design your own luxury all-electric car at Santana Row’s Tesla store.

Your next destination is a deeper dive into the towns and tech campuses of the Silicon Valley.

Next Stop
Silicon Valley (15mi/24km; 19 min)
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Silicon Valley

Silicon Valley
If you don't believe us, just Google it

Welcome to California’s tech-centric brain pool. Wrapping around the south end of San Francisco Bay, the communities collectively known as Silicon Valley are home base for the heart and soul of computer technology, including silicon chip technology, computer design, apps and Apples, smart phones—smart everything. Some companies are so big and so influential that their names have become part of our vocabulary (if you don’t believe us, just Google it). Hike or bike a trail and overhear the next big idea. Visit a museum that blinks and buzzes with what-if technology. And enjoy the riches of a booming economy, with performance spaces, high-end shopping, and multi-starred restaurants.

Companies like Facebook and Google don’t have formal tours, but at the Googleplex campus in Mountain View you can witness the “Googlers,” alarmingly youthful employees talking, tweeting, and riding signature Google bikes on their way to changing the world. Head to the east side of the campus, along the paved bike path, to look down on manicured playing fields that are the exclusive domain of employees. What you can’t see (but wish you could) are the campus’s gourmet-food-for-free cafeteria, on-site masseuses and daycare center, and assorted nap pods—a Eutopic campus on the edge of San Francisco Bay.

Just south in Cupertino, pick up logo t-shirts, baseball caps, and mugs at another legendary campus, Apple, at One Infinite Way.

North in Menlo Park, the Facebook campus continues to expand. It’s also closed to visitors, but the sign out front—the iconic, thumbs-up “like” in baby blue—has become a popular backdrop for selfies. You can do it too: just pull over, smile, click, and post.

And then there’s the modest building where it all began: the shed/garage at 367 Addison Avenue, Palo Alto, where, in 1939, Bill Hewitt and Dave Packard forged a partnership that would become the global tech powerhouse known as HP.

Once you’ve got your fill of technical wizardry, head south (just like locals do on weekends) to the coastal town of Santa Cruz, best known for its broad beach and waterfront amusement park.

Next Stop
Santa Cruz (38mi/61km; 45min)
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Santa Cruz

Santa Cruz
Surf's up at Norcal's friendly beach getaway

Follow Highway 17 south over the rugged Santa Cruz Mountains toward the coast, where you can relax and play in this ultra-mellow beach town. Santa Cruz has a decided split personality—and both sides are cool. First, there’s the woo-hoo family fun of the Santa Cruz Beach Boardwalk, a yesteryear-style esplanade lined with classic coasters, arcade games, corn dogs, and a historic carousel. Then there’s downtown Santa Cruz, where local college students browse for vintage and boho chic, and relaxed restaurants focus on organic, local ingredients.

But at its heart, Santa Cruz is a surf town. This is where the sport was originally introduced in California, and top surfers know that the place to be is Steamer Lane. Need more proof? Nearby lives Jack O’Neill legendary surfer and force behind the O’Neill empire, pioneer of the wetsuit and elder statesman of everything surf in the Golden State. 

A wide beach and splashable waves are always inviting; add a colorful boardwalk with rides, games, and music—well, how can you say no? Not many people do—this popular waterfront boardwalk is a summertime ritual for countless California families, a wonderful way for you to relax and play just like the smiling locals. While there are countless attractions lining the boardwalk, the big star is the Giant Dipper, a burly wooden coaster first opened in 1924 and generating screams, squeals, and squinched-shut eyes for decades. These days, it’s not the only thrill ride in town; the boardwalk also features the 125-foot/38-meter-high Double Shot tower for heart-in-throat adrenaline lovers. For tamer rides, especially for little ones, take a spin on the painstakingly restored 1911 Looff carousel (yes, that’s real horse hair in the tail of your painted steed).

Your road trip ends back in San Francisco, where you can explore by foot, bike, or clanging cable car.

Next Stop
San Francisco (73mi/117km; 1hr20min)
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San Francisco

San Francisco
Sparkling Bay, Magic City

End your road trip by exploring one of the world’s great cities. Famous for grand-dame Victorians, classic cable cars, dynamic diversity, a beautiful waterfront, and a soaring crimson bridge, the “City by the Bay” truly has it all. 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-sees on a traveler’s wish list.

For a novel way to explore, park your car and explore by foot, bike, and unique public transportation. Pedal bikes across the Golden Gate Bridge and back, then explore the lush Presidio, a former military base that’s now a park, or head into Golden Gate Park to visit museums and row across a secret gem, Stow Lake. Continue along the flat Embarcadero to Fisherman’s Wharf and the Exploratorium science and learning museum.

Return your bikes and hop a cable car to ride over the hill to the high-end shops and enormous Macy’s, Niketown, Saks Fifth Avenue, and Neiman Marcus around bustling Union Square, with a stop for Italian pastries and cappuccino at Emporio Rulli right in the square. Nearby, stroll boutique-lined Maiden Lane—pedestrian only thoroughfare during the day, when cafes set up tables and chairs right in the street. Nearby Westfield Mall, a dazzling complex on once scruffy but now spiffed up Market Street, glitters with even more stores, including an deluxe food court on the lower level. At night, catch a show in the theater district, or head to North Beach to see Beach Blanket Babylon, a raucous and irreverent San Francisco institution. For more nightlife and dining, stroll Valencia Street in the Mission, a trendy and eclectic hotbed of restaurants and bars, and awesome late-night scoops at Bi-Rite Ice Cream.