With a vibrant downtown, fascinating neighborhoods, and a buzzing beer and wine scene, San Jose makes for a festive—and supremely easy—weekend getaway. Here’s how to plan out an action-packed itinerary in this Silicon Valley hub, complete with culture, fine dining, and retail therapy.
Friday
Check in at your hotel.
Downtown San Jose, with its wealth of alluring places to stay, makes an excellent launching pad for exploring the city. Not only are downtown hotels close to the city’s biggest museums and venues, but they also offer easy access to the city’s light rail system, so you can efficiently explore the city without driving the whole time.
These hotels are loaded with charm too, whether modern or historic. The 22-floor Signia by Hilton San Jose, for instance, sits across from Plaza de César Chávez Park and offers contemporary stylishness, while the nearby Westin San Jose is housed in the home of the 1925 Saint Claire Hotel. For a boutique-style stay, consider the Hotel Clariana, a 44-room, Beaux-Arts property that dates back to 1913 and is now listed on the National Register of Historic Places.
Enjoy a local happy hour.
Enjoy Friday afternoon downtown at brewpubs and bars that highlight the local beverage scene. Start with the award-winning Triple Play IPA and the Big Wall Imperial Stout at the baseball-themed Strike Brewing Co. or pull up a stool at Market Beer Co.’s taproom with 30 beers on draft, more than 200 bottle and can options, and frequent pop-ups from local brewers.
The nearby Fox Tale Fermentation Project serves up more local beer, kombucha, and even fermented foods like sauerkraut and kimchi made with local produce. For an artisanal cocktail, head to Paper Plane where you’ll find a long list of bottles (absinthe, pisco, and Japanese shochu) as well as creative cocktails such as the Smuggler’s Haunt (scotch, Madeira, and dry vermouth).
Take an evening stroll to dinner.
Just a few blocks’ walk from your downtown hotel, San Pedro Square offers both history and a mellow atmosphere that encourages spontaneity. The heart of the square is Peralta Adobe, a 1797 home that was part of the city’s El Pueblo de San José de Guadalupe settlement. Today, the surrounding buildings offer more than 20 food and drink options, along with live music wafting through the air. Consider sit-down options such as the shareable plates at District and the Mexican cuisine at Olla Cocina, or browse the offerings at the food-hall-style San Pedro Square Market, including Jora Periuvian, Hella Good Burger, and the Gelato Shop.
Saturday
Power up for the day.
Make the most of the downtown’s business community—and its serious java drinkers—when choosing your breakfast. You have a wide range of acclaimed coffee options, including the fair-trade beans at Voltaire Coffee Roasters, the sustainability-minded menu at Academic Coffee, and the creative drinks—like the sweet potato pie latte—at Nirvana Soul. Sit down for a south of the border–style omelet at Tostadas or sip one of the “destination lattes” (like the Santiago, with red rouge cocoa and cayenne) at Voyager Craft Coffee in San Pedro Square. Or head into neighboring Japantown to experience the beloved Mobil-station-turned-coffee shop Roy’s Station.
Pick a neighborhood to explore.
San Jose is comprised of nearly 20 distinctive neighborhoods, each with its own historic spots, boutiques, and cultures. Little Saigon, for instance, is home to the largest Vietnamese community outside Vietnam, while the city’s Little Portugal is one of the rare Portuguese communities in the U.S. Walk though Japantown—check out the public murals and benches along Jackson Street, and then stop in at the Japanese American Museum of San Jose—to learn about the community that has been here for more than a century.
Neighborhood explorations offer easy stops for lunch, such as sushi at Minato, the Portuguese bifanas at Bacalhau Grill, or pho at Little Saigon’s Bun Bo Hue An Nam. In the city’s Rose Garden neighborhood, meanwhile, you can literally stop to smell the roses— 4,000 of them—at the 5.5-acre Municipal Rose Garden. Afterward, enjoy a gyro and a banana shake at longtime local favorite Falafel’s Drive-In.
Consider a game day.
Depending on the time of year, you could easily build a weekend afternoon or evening around a game in the San Jose area. The NFL’s 49ers play at Levi’s Stadium in Santa Clara, a short light rail ride away from downtown. During summer and fall, you can stay in town to watch the NHL’s Sharks play at the SAP Center (aka the Shark Tank), or see the San Jose Giants play minor league baseball at Excite Ballpark. From February through October, Major League Soccer’s San Jose Earthquakes and the National Women’s Soccer League’s Bay FC play at PayPal Park.
Sports enthusiasts should check out the mural and merch at World of Sports Memorabilia or watch games and dine at fan-friendly spots such as Alex’s 49er Inn in West San Jose and Rookies Sports Lodge and O’Flaherty’s Irish Pub near the Shark Tank.
Go wine tasting.
Thanks to its proximity to three American viticultural areas—Livermore Valley, the Santa Cruz Mountains, and Santa Clara Valley—San Jose offers abundant world-class wine within a short drive. One don’t-miss stop for wine lovers: The acclaimed Monte Bello Estate at Ridge Vineyards, 20 miles away in Cupertino.
You can also get a sense of the local terroir right in town. Start with Sauvignon Blanc and Cabernet Sauvignon at the award-winning Alamitos Vineyards, housed in a former quicksilver mine in the Almaden Valley neighborhood. Then head to the quaint Alameda neighborhood to taste the Pinot Noirs at Coterie Winery and the small-lot and single-vineyard wines at J. Lohr’s San Jose Wine Center.
Enjoy dinner and a show.
Whether you want to experience the local symphony, a touring Broadway show, or a cutting-edge theater group, an evening of engaging culture awaits in San Jose. Downtown is home to several historic and beautiful venues, including the California Theatre (a 1920s movie theater that is now the place for ballet or opera), the Mission-style San Jose Civic, the Montgomery Theater, and San Jose Center for the Performing Arts, a1972 building designed by the Frank Lloyd Wright Foundation. Downtown also boasts the San Jose Improv, housed in a 1904 Art Deco building, and the multi-venue 3Below, which hosts cheeky shows and screenings such as a Dirty Dancing dance-along.
Given the venues’ convenient locations, it’s easy to enjoy an excellent pre-show dinner downtown. Choose from options such as acclaimed Portuguese restaurant Petiscos, the sustainable seafood at Scott’s Seafood San Jose, or the “pasture-to-plate ” cuisine at Orchestria Palm Court, located in a 1910 building decorated with antique musical instruments. After the show, grab a nightcap at Guildhouse, a bar stocked with board games, or enjoy cocktails and vinyl records at the bar Still O.G.
Sunday
Sit down for a local-flavor brunch.
Brunch is another low-key way to soak up San Jose’s neighborhood ambience. Tree-lined Willow Glen, for instance, boasts pretty architecture, boutiques, and brunchy favorite The Table, with frittatas, Benedicts, and ricotta beignets. For breakfast with a side of photo ops, check the calendar for open dates at Asian-French fusion K Café Patisserie and Tea House in West San Jose, or feast on crepes at downtown’s Whispers Café. Want a classic dim sum? Head to Dynasty, located inside Little Saigon’s Grand Century Shopping Mall.
Make learning fun at a museum or historic spot.
Tap into the tech smarts and creative energy of Silicon Valley by exploring a museum or two. Learn about the area’s innovative roots at The Computer History Museum, then get hands-on with science exhibits at The Tech Interactive. In the same spirit, the San Jose Museum of Art focuses primarily on contemporary art.
For more fascinating local history, check out the house where César Chávez once lived, or head to Kelley Park to see more than 30 original and reproduced homes and buildings from San Jose’s early days, including a trolley and candy shop. Another don’t-miss is the Winchester Mystery House, the 160-room Victorian mansion that has both a bizarre layout and a fascinatingly creepy history—perfect for anyone who loves to celebrate Halloween year-round.
Finish the weekend with some retail therapy.
Immerse yourself in one more classic San Jose neighborhood by strolling the row house–lined streets and browsing the shops of Santana Row. The shopping hub’s 50-plus stores and restaurants include jeweler Kendra Scott, home design icon Herman Miller, and fragrances of La Labo.
Finally, toast the weekend that was at Vintage Wine Bar, which offers 25 different wines by the glass. It’s a great spot for leisurely people-watching along Santana Row, and then purchasing a few bottles to take home.
