wineries

Day Trips and Sips: Pair a Hike with a Winery on Cupertino’s Montebello Road

Vineyards adjacent to the Water Wheel Parking Lot, Montebello Road. Photo by Ben Lilly.

By Ben Lilly

Jan. 2, 2024 (Updated Dec. 24, 2024)—Hilltrompers, we have good news: you don’t have to schlep to Napa or Sonoma to enjoy a day brimming with rural landscapes and local wines. Instead, just hit the vineyards of Cupertino.

Day Trips and Sips: Explore Ancient Oaks and Savor Sustainable Wines Along Skyline Ridge

The Ancient Oak Trail brings you to one of the most stunning Live Oak groves in Northern California. Photo by Majken Talbot.

Explore the trails of Russian Ridge, enjoy a lunch at Alice’s Restaurant, and soak up the views from the crest of the Santa Cruz Mountains while wine tasting at the Thomas Fogarty Winery.

Day Trips & Sips: Downtown Los Gatos & the John Nicholas Trail

Katie MacCafferty literally jumping for joy under the redwoods on the John Nicholas Trail. Ben Lilly photo.

One of Silicon Valley’s most charming downtowns offers excellent coffee options, great beers & wines, and proximity to an unforgettable trail in the redwoods.

Day Trips and Sips: A Coastal Hike and Barnyard Fun in Half Moon Bay and Pescadero

The accessible Cowell-Purisima Beach Coastal Trail features gorgeous views atop steep cliffs. Photo by Alina M. Darkhovsky/Shutterstock.

A visit to the Cowell-Purisima Beach Coastal Trail and the Harley Farms Goat Dairy, with a nice Cantina lunch and wine tasting at Sante Arcangeli Family Wines.

Santa Cruz Mountains AVA: California’s Lesser Known Wine Region

Wine tasting at Mindego Ridge vineyard, Alpine Road, La Honda. Credit: Mike Kahn

When we think of wineries near the Bay Area, Napa and Sonoma tend to dominate the conversation. But did you know that there are wineries producing world-class wine in the Santa Cruz Mountains?

Day Trips and Sips: Explore Big Basin as it Rebuilds

Big Basin Redwoods State Park welcomes visitors after the CZU Lightning Complex Fires in 2020. Credit: Naomi Friedland

Big Basin and the surrounding Santa Cruz Mountains area have a lot to offer, from hikes showcasing the resiliency of redwoods after the 2020 CZU Lightning Complex Fire to rustic wineries and well-loved dining establishments.

Day Trips and Sips: Wine Tasting, Hiking and Food in Portola Valley

Sunrise from Windy Hill overlooking San Francisco Bay, copyright Eleanor Raab.

Enjoy a great Portola Valley day trip adventure drinking coffee at Konditorei Cafe, hiking or mountain biking at Windy Hill Open Space Preserve, wine tasting at Neely Winery, and grabbing a bite or a beer at Alpine Inn. Ooh, game on!