Silicon Valley Wineries & Winter Parks: A Relaxed 3-Day San Jose Itinerary for Wine and Nature Lovers

Cold air hits first when you step out at Alum Rock: that mineral smell from Penitencia Creek, eucalyptus leaves slick from last night’s drizzle, the quiet crunch of gravel under boots while the city hums somewhere far below. Morning here feels almost private—just you, the regulars who’ve been walking these trails for decades, and the way the light slides slowly down the canyon walls. By late morning you’re trading creek chatter for the soft echo of a working winery: Coterie’s barrels lining a warehouse space off West Julian, the faint whir of equipment, and the warmth of a pour explained by someone who actually made it. After lunch, the day loosens. Guadalupe Oak Grove Park is all tawny hills and gnarled branches, the sound of acorn woodpeckers tapping away as you follow narrow paths through dry grass brushing your calves. Evening pulls you back into human scale: Lamella Tavern’s low light on Lincoln Avenue, the cool brine of oysters against a winter chill you barely feel through the glass, then a short hop to Little Wine House where candles, crusty toasts, and murmured conversations replace the day’s wind. You go to sleep with trail dust still on your jeans and a very local pinot noir still on your mind, already curious how the mountains will behave tomorrow.

The second morning smells like wet bark and cold stone. At Castle Rock State Park, you step onto the trail and immediately feel the temperature drop under redwood canopy, the air thick with the quiet drip of last week’s rain and the earthy tang of decomposing leaves. Rock formations loom beside the path, pocked and sculpted, while occasional openings reveal slivers of the valley below, pale in the winter light. It’s less a workout and more a moving meditation, your boots scuffing against roots and sandstone as you follow loop trails that locals swear by for a quick reset. By midday, the mood shifts to leisurely hedonism. At MJA Vineyards’ Westside tasting room in Santa Cruz, reggae might be playing softly, heaters warming the patio while flights of cabernet and syrah arrive with a side of Hawaiian coffee if you’re pacing yourself. The afternoon stretches at Windy Hill Open Space Preserve, where open grasslands and switchbacking trails give you big-sky views all the way to San Francisco on a clear day, the wind tugging at your jacket and the smell of dry grass in the air. Evening belongs to Los Gatos: VinoVero’s candlelit interior, where Italian bottles line the walls and plates arrive from a compact kitchen, and then Winston Champagne Bar, a tiny bubble-forward room where flutes catch the light like jewelry. Tomorrow will pull you back closer to San Jose proper, but today is about the pleasure of distance.

Your last morning starts not with a white cube gallery but with Bill’s Backyard, the outdoor wing of the Children’s Discovery Museum where interactive installations and playful structures catch the early light. It’s technically built for kids, but the colors, textures, and oddball contraptions have a way of disarming adults too—metal, wood, and plastic warmed by the sun, the distant sound of light rail passing as families’ laughter drifts across the space. From there, the day tilts uphill, literally, as you wind your way to Bella Montagna’s hillside estate where the city falls away and the air smells like warm stone and trimmed vines. Afternoon stretches into a drive deeper into the Santa Cruz Mountains to Wrights Station, where rows of vines contour the slopes and the tasting patio feels like a front-row seat to the weather rolling over the ridgeline. The light softens as you head back toward town, pausing at the Villa Montalvo Lookout Point for a last hit of golden-hour drama over Saratoga. Dinner lands you at The Hero Ranch Kitchen, where wood, leather, and a confident menu feel like a grounded exhale after days of movement. The finale is downtown again, but not in a chaotic way: Goodtime Bar’s Fountain Alley patio with its serious wine list, small plates that overdeliver, and the low buzz of a city that’s already thinking about Monday. Tomorrow you’ll go back to your regular life; tonight, you’re still in the valley of vines and winter greens.