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Loving Los Gatos

A three-Michelin-star restaurant, an outdoor jazz festival, and a historic winery await visitors to the South Bay’s crowning jewel.


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The four-star Hotel Los Gatos blends comfort with class. Photo courtesy of Greystone Hotels.

A getaway to Silicon Valley may not sound like the most enticing proposition. But picturesque Los Gatos—a chic enclave nestled in the foothills of the Santa Cruz Mountainsdefies expectations with its superb shopping, lively entertainment, and outstanding food and wine destinations. A one-hour drive down Highway 880, which turns into Highway 17 just past San Jose, will get you there.

EXPLORE

Shoppers will delight in North Santa Cruz Avenue, with its array of fashion-forward boutiques, home-decor showrooms, and other eclectic stores. Don’t miss local designer Jennifer Croll’s eponymous shop, which specializes in little black dresses. For young children, there’s an imagination-inspiring toy store called Automobuild—and kids of all ages will go wild for the rare candies at Lolli and Pops

If shopping isn’t your thing, head to the New Museum to discover art exhibits exploring timely topics as well as history presentations about the area. Alternatively, you can stroll along the 10-mile Los Gatos Creek Trail, which winds from Old Town to Oak Meadow Park, with its historic mini steam train, the Billy Jones Wildcat Railroad. , , , , .

DINE

Chef David Kinch put Los Gatos on the culinary map with Manresa, his three-​Michelin-star restaurant. The fine-dining mecca—which serves an ever-changing tasting menu comprised of impeccably prepared, locally sourced ingredientsis an extraordinary experience for any food enthusiast.

If you can’t get a reservation at Manresa, head to Kinch’s more low-key eatery, The Bywater, a joyful paean to the chef’s hometown of New Orleans. In conceiving the place, Kinch—whose parents live in Alamo—says he tried to create a neighborhood restaurant “where I’d want to hang out.” The ambience is festive, and the food is hearty, homey, and intricately spiced. (Think fried chicken, gumbo, and po’boys; fresh oysters prepared several ways; and the requisite Louisiana dessert: beignets.) As in New Orleans, cocktails take center stage: Sip a Sazerac or Hurricane, and drink in the relaxed atmosphere of The Big Easy. , .

Testarossa Winery's Cellar 1 provides a chic setting for events. Photo courtesy of Testarossa Winery and Tasting Room.

ENJOY

After lunch, take a short drive up the hill to discover Testarossa Winery, a family-owned operation housed in a 130-year-old Jesuit seminary. Wander into the cavelike tasting room to sample exceptional Pinot Noirs and Chardonnays—and a limited-edition rosé, which debuted in May—or sit out on the patio of the winery’s Wine Bar 107, which hosts live music on Thursdays, Fridays, and Saturdays.

For more musical thrills, don’t miss Jazz on the Plazz—a free outdoor performance series that brings world-class musicians to Los Gatos Town Plaza from June 13 to August 22. As a bonus, Grammy Award–winning R&B singer Aaron Neville headlines this year’s Los Gatos Music and Arts fundraising gala on June 26. Buy your tickets now! , jazzonthe plazz.com.

David Kinch's shrimp and avocado remoulade is a Bywater specialty. Photo courtesy of The Bywater.

STAY

With so many enticing options in Los Gatos, why drive home right away? Check in to Hotel Los Gatos, a refined retreat modeled after a Tuscan villa, offering 72 luxurious guest rooms. Most feature balconies, and all include Egyptian cotton linens, sumptuous robes, and in-room tablets you can use to order room service or call your car from the valet. Take a dip in the pool or hot tub, or indulge in a customized therapeutic massage at the on-site Verde Touch spa. (Tip: Book spa services well in advance.)

Hotel Los Gatos is also home to Dio Deka, an acclaimed Greek restaurant that elevates Hellenic classics such as saganaki—nut-​crusted Feta served over farro and roasted beets dressed with a sweet wine sauce—and features a selection of prime mesquite steaks from the esteemed purveyor Allen Brothers.

Before checking out, say goodbye to the gracious staff, and bid a fond farewell to your 24 hours in lovely Los Gatos.

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