Perhaps Silicon Valley’s strangest and yet most enduring attraction is Winchester Mystery House, a 160-room Victorian mansion that was owned and built by Sarah Winchester, heiress to the Winchester fortune. Construction began on the house in 1884 and continued, almost nonstop, until 1922—racking up a bill of $5.5 million. Why the unending, breakneck pace? Because Sarah had been convinced by a medium that all the spirits of the people killed by Winchester firearms had placed a curse on her family and would haunt her forever unless she moved West and built a house to match their specifications, as revealed to her in séances.
Whether spirits gave her pointers or not, Sarah designed one heck of an oddball house. Guided tours let you ponder the heiress’s unusual designs, including doors that open onto blank walls and a stairway that leads straight into a ceiling. Other weird facts: the mansion has 52 skylights, 47 fireplaces, 40 bedrooms, 40 staircases, 13 bathrooms, 6 kitchens, 3 elevators, 2 basements, and 13 bathrooms but just one shower.
The first hit of this city’s unmistakable techy-ness starts right off the bat—if you get here by plane. Meet Space Observer, a 26-foot/7.9-meter-high white-and-chrome robot that welcomes you to Terminal B at ultra-modern Norman Y. Mineta San José International Airport. But even if you don’t get the meet-and-greet from the big guy at the airport, you’ll find plenty of other ways to experience the dramatic rebirth of California’s third largest city as the Silicon Valley’s urban hub. Downtown 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.
As the cultural center of Silicon Valley, San Jose is the land of innovation, startups, and technology history. Just a stone’s throw from some of the most pioneering businesses ever founded, you can find intimate opera performances and three-star Michelin dining. Here’s how to see a different side of San Jose.
Stay at the luxurious Hotel Valencia
Feel like an Andalusian aristocrat at Hotel Valencia, the only hotel on the city’s Santana Row, home of some of the city’s best shopping and dining. Architectural touches, inspired by Old World Spain, include a fountain-filled veranda, complete with fire pits when it’s time to get cozy.
Explore Winchester Mystery House
The product of a fascinating architectural undertaking, the Winchester Mystery House is a must-see. In 1886, Sarah Winchester, the widow of a firearms magnate, began construction on her home—a project that continued for 36 years, ending only with her death. Learn more about the eccentric millionaire and explore her home’s peculiar quirks—including 2,000 doors, staircases leading to nowhere, and a cabinet that opens to dozens of rooms.
Taste at the historic Testarossa Winery
Built in the 19th century by Jesuit Brothers, the Novitiate Winery in neighboring Los Gatos is one of the oldest in California. Its stunning cellars are now the home of Testarossa, where you can enjoy wine tastings, cheese pairings, and live music Thursday through Sunday.
Watch the Opera San José
Since Opera San José is the country’s only year-round company of principal artists, you can delight in arias any time of year here. Enjoy classics like Cosi Fan Tutte or The Flying Dutchman with the beautiful California Theatre offering a baroque-inspired backdrop.
Eat at Manresa
Tucked away in neighboring Los Gatos, Manresa is a member of the hyper-exclusive Michelin-three-star club. Chef David Kinch expertly crafts the season’s best products into a first-class, prix fixe experience: Think Hokkaido uni, Riesling-poached pears, and slow-roasted squab. If you can’t snag a reservation, sample his genius at Manresa Bread, which offers confections such as fluffy chocolate croissants and the perfect Pullman loaf.
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San Jose is home to more than a dozen museums, including downtown’s lovely San Jose Museum of Art. Families will especially love the Tech Museum of Innovation, which features collaborative exhibits with Silicon Valley’s biggest brands, and the Children’s Discovery Museum of San Jose, with its full-size firetrucks and giant bubbles.
Kids get to learn about science in real-life ways—from fossil-digging to bubble-blowing and gardening—at the Children’s Discovery Museum of San Jose. The location alone offers some serious Silicon Valley street cred: The distinctive purple building sits on downtown San Jose’s Wozniak Way—known by locals as “the Woz,” and named after Apple co-founder Steve Wozniak.
First opened in 1990, the museum houses roughly 150 exhibits, ranging from classic displays to interactive real-world applications, and geared to kids as young as infants (the sweet spot, though, may be elementary-school age). Start by checking out Lupe, the replica of a woolly mammoth—whose real fossils were found in Silicon Valley—then take to the neighboring dig pits to learn how archeologists search for fossils. In other areas, kids can make art, blow giant bubbles with bubble rings, play with worms to learn about composting, and explore the mathematical magic of circles.
“Parents love the opportunities that the museum provides for family learning, whether it’s seeing who can create the biggest bubble, sparking scientific inquiry in Mammoth Discovery, or unleashing a misty cloud of fog in WaterWays,” says museum spokesperson Cecilia Clark. And reflecting the diverse community of Silicon Valley, the exhibits feature trilingual signage: English, Spanish, and Vietnamese.
As of fall 2017, the museum is stretching outdoors. Its half-acre “Bill’s Backyard: Bridge to Nature” invites kids to get their hands dirty, whether they’re digging in the dirt and planting seeds, tree-climbing, or pumping water out of a rain catchment system.
“Regardless of ability, age, or access, adults love that their children take the lead in exploring in a safe, welcoming, and enriching environment,” says Clark. Snack time is rewarding too: The museum’s FoodShed offers fresh and minimally processed foods—like sweet potato quesadillas, whole-grain-bread sandwiches, and German apple cake—all low in sugar with no additives or preservatives.
Think of this extraordinary complex, at Kelley Park, as the Santa Clara Valley’s memory book in real life. It’s a chance to imagine what the region was like before computer chips, gigabytes, and tech startups became the heartbeat of the region. First, there are expansive displays and historical buildings (imported to the park campus) that showcase the region’s amazing agricultural roots, including historical images, machinery, and other mementos. Other buildings shed light on various early trades and businesses, such as a recreated print shop, where costumed volunteers let kids try out an early printing press. For a fascinating look at the broad range of immigrants who have settled in the region, tour the collection of preserved buildings—from early banks to a former stable—that make up History Park. This cultural campus provides a place for 19 partner programs to tell their history, like the harrowing journeys made by Vietnamese boat people, and share their traditions at lively festivals, like the annual Dia de Portugal.
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”—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 this snazzy outdoor mall, a mix between California’s relaxed stylishness and a swanky European village on market day. This walkable, nook-and-cranny-filled complex has benches for relaxing under leafy oaks, large sculptures by French artists André Dumonnet and Christine Foulché, antique fountains, live musicians, and open-air seating outside quality restaurants. 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. If your shopping tastes run more toward Main Street than Paris boutique, there are familiar chains including Orvis and H&M. And, in the ultimate Silicon Valley indulgence, why not custom-design your own luxury all-electric car at Santana Row’s Tesla store.
After decades in a foggy, chilly wind tunnel known as Candlestick Park, the San Francisco 49ers football team has moved south to one of the snazziest stadiums around. Players now huddle, punt, and play in 68,500-seat Levi’s Stadium, a high-tech marvel northwest of downtown San José. The stadium, slated to host Super Bowl 50 in 2016, also boasts eco-friendly features like a living roof, solar panels, and field irrigation that uses recycled water. If you’re lucky enough to settle into a luxury suite, check out the woodwork: it’s made of sustainable bamboo.
Befitting a stadium in the heart of Silicon Valley, Levi’s Stadium is also high-tech to the max, with fan-friendly touches like Wi-Fi access in every seat, so you can tweet, post, and chat about the game, not to mention order food without missing a play. If you do venture out to eat, it’s not all lukewarm hot dogs and soggy fries. Celebrity chef Michael Mina overseas the stadium’s high-end steak house, which offers inside-the-park tailgate parties throughout the season.
Beyond football, the venue is slated to host college football games, domestic and international soccer matches, motocross events, concerts, wrestling, and more. Public tours of Levi’s Stadium and its new 49ers Museum let you check out all this fabulousness, even if you’re not going to a game or event. The stadium also makes it easy to use public transit, with close-by access to local light rail, bus, and Caltrain.
In a city where tech is king, it makes sense that artists here get influenced by edgy new techniques and sounds. Check out the results at June’s SubZERO Festival, with artists, musicians, and other artisans showing their stuff. Young techies flock to September’s C2SV (Creative Convergence Silicon Valley), a showcase for indie bands.
The region’s rich ethnic mix fuels high-energy festivals such as Viva Fest: Mexican Heritage & Mariachi Festival (events held July through October), and July’s Obon Festival in Japantown. Some events just aim to make people smile, like the seasonal favorite, Christmas in the Park, celebrated downtown at Plaza de Cesar Chavez. Wander through a winter wonderland of lights, snowmen, trains, and other holiday themes. The highlight is an enchanted forest of trees decorated by local schools, community groups, and businesses.
This downtown museum prides itself on its origins: In 1969, the beautiful 19th century building that then housed a library was threatened with demolition, and a group of citizens banded together to save it and open an art gallery. That local effort grew, creating this remarkable downtown facility, including a light-filled wing added in the 1990s. Permanent exhibits present an outstanding and varied collection, including contemporary abstracts, photography, figurative painting, sculpture, and works in new media by Bay Area artists. If you’ve got kids, check the schedule for family-friendly, hands-on activities to help children get excited about art.
Culture hounds have plenty to do in California’s third largest city. Downtown, the San Jose Center for the Performing Arts hosts Broadway traveling productions, as well as a full calendar of international artists. Ballet San Jose also graces the stage here. Big names are often the draw at the handsome City National Civic; The Who kicked off their first headlining U.S. tour here in 1968, and other big stars, including Barbra Streisand, The Rolling Stones, and Frank Sinatra have all performed in this beautiful space, which debuted a multi-million dollar renovation in 2012.
The 1927 California Theatre, originally a grand movie palace, creates a lavish backdrop for performances by Symphony Silicon Valley and Opera San Jose, presenting classical works and chorale events. Even if you don’t step inside the beautiful theater, take special notice of the marquee out front. It’s decorated with a motif of California poppies, based on historic drawings and photographs, and meticulously recreates the look, size, and detail of the theater’s original sign.
For plays and musicals performed by local companies, check the schedule at the1936 Montgomery Theater, an intimate and elegant venue.
San Jose’s vibrant dining scene is one of the Bay Area’s best-kept secrets. In recent years, dozens of excellent restaurants, breweries, and wine bars have opened their doors in the so-called Capital of Silicon Valley.
San Jose serves up exceptionally elevated dining experiences. In 2018, Adega became the first restaurant in the city’s history to receive a Michelin star—one of only two Portuguese dining spots in the country to ever receive that honor. Three different prix fixe menus (splurge for the seven-course tasting menu) are offered daily at the family-owned establishment. Celebrity chef Michael Mina, a Michelin-star winner in his own right, works his magic at Arcadia, a steakhouse that’s a popular spot before or after shows at the nearby San Jose Center for the Performing Arts.
Think of a global cuisine and you’re almost sure to find it in San Jose. Enjoy a kaleidoscope of authentic international flavors, including traditional Ethiopian fare at Zeni Restaurant and homemade tarmosalata at Nemea Greek Taverna. With more Vietnamese residents than any city outside of Vietnam, San Jose is a hotspot for pho, bahn-mi, and banh xeo—all of which can be found at Grand Century Mall in Little Saigon. If American-style meat and potatoes is what you’re after, head to Harry’s Hofbrau for an old-fashioned buffet paired with specialty craft beers.
Downtown San Jose’s lively, open-late food hall, San Pedro Square Market, is a great place for a casual hang or a grab-and-go meal. How about a bowl of Nepali steamed dumplings from Urban Momo? A glass of wine from local vintners at Vino Vino? Check out Treatbot, the ice cream trike from the future, serving up karaoke and local ice cream flavors like the “408” (caramel ice cream, fudge, and Oreos). No sense goes un-served in the public market’s three halls: Keep your nose peeled for the aroma of roasted coffee beans and wood-fired pizza, while enjoying live entertainment and local artwork.
On sunny days (which are the norm here), take your food out to a table or bench in the adjacent plaza, bordered by the Peralta Adobe (the city’s oldest building; guided tours are offered throughout the year).
Alongside its outstanding eats, San José is making a name for itself in the craft brew scene as well. Following the Silicon Valley creed of “iterate, iterate, iterate,” Hermitage Brewing brews three or four beers almost every single day. Strike Brewing Company marries a sports bar feel (pretzels and ping pong) with upscale Belgian-style beers. At local favorite Good Karma Artisan Ales & Café, you can sip carefully crafted lagers alongside the best vegan food in the South Bay. Enjoy!
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...