How to get the most out of a long weekend in California wine country.

By Zach Dundas
March 22, 2021
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The following is an excerpt from Wildsam's latest book, WILDSAM Napa & Sonomawhich leads travelers into the heart of California's wine country with guidance from trusted locals and wine experts. Check recommended venues for COVID-19 updates before visiting.

When it comes to Northern California wine, ancient earth-building intersects with the latest marketing trends. Behind bold-face reputations and a glossy surface lies a true farming culture stitched from hard work, generational knowledge and expert craft. While editing our new book about Napa & Sonoma, we looked for destinations that embodied the region's roots and the deep pursuit of wine.  

Vineyards in Napa Valley, Northern California
Credit: TraceRouda / Getty Images

The beauty of Napa and Sonoma counties is that you can visit many times over and never experience the region (or the wine) the same way twice. You can define your personal favorite spots, and craft your own schedule. For the first-time explorer, we took some of our must-visit destinations and created a three-day-weekend itinerary for anyone seeking a deeper sense of place and the stories of interesting people behind the vines.

Day 1: The Yountville Ride

Before moving into open spaces toward the coast, start with exploring the cities' centers. To see real Napa at its most vivid, hop on two wheels or explore on foot through the Napa Valley Vine Trail. This section covers 12.5 miles through the city of Napa's working-class roots, into the tumble of verdant vineyards that line Highway 29 until reaching Yountville's luxe center. Rent rides from Napa Valley Bike Tours in downtown Napa, then cruise a couple blocks to La Esperanza Tacos for exceptional handmade street food. Just a block away, the Vine Trail picks up next to St. Clair Brown Brewery and Winery, a handy early hydration stop and rare crossover: Elaine St. Clair stakes a claim as the nation's only woman working as both winemaker and brewmaster. Pedal alongside the tracks of industrial Napa, eyes peeled for murals.

The trail straightens out at the scenic Oak Knoll section, where wine country's bucolic fantasy quickly percolates into the small-town reality. To your right, iconic wineries (Ashes & Diamonds and Trefethen) dot Highway 29; to your left, rows of vines serrate the valley floor. As Ashes & Diamonds founder Kashy Khaledi says, "The winery is a reaction to what Napa Valley became. It's also a love letter to what it was." Pull off at Elyse Winery, a disarming setting for small-production zins and cabs from serious heritage vineyards. As the oak-shaded route bends into Yountville, pass the French Laundry Gardens, and wind up on Washington Street, Yountville's epicenter of the good life. Stop at Jean-Charles Boisset's rococo Atelier Fine Foods for outrageous luxuries (caviar, foie gras) and Bouchon Bakery for coveted macarons.

Put your name in at Ciccio, Yountville's Italian charmer. Its repurposed market building boasts vintage Italian movie posters and handwritten butcher paper menus for a festive, unpretentious evening. Drink a negroni while you wait on Neapolitan pizza and crispy-skinned whole branzino. Too late to bike back? No problem–for a $20 fee, return your bike to Napa Valley Bike Tours' Yountville outpost, then call for your chariot (which may just be an Uber but could well feel like a chariot by now).

Napa Valley illustrated map
Credit: Illustration by Liana Jegers

Day 2: The Carneros Point-to-Point

Foggy bay breezes create a cooler climate perfect for pinot and chardonnay—and a welcome break from Napa Valley's spicier heat. For a satisfying arc, drive west to east from the Sonoma County side. On Highway 21, visit Cornerstone Sonoma, where Sunset magazine's test gardens grow amid boutiques and tasting rooms. Angelo's Wine Country Deli (spot the rooftop cow) can supply a classic sandwich.

Heading eastbound on Highway 12 to Denmark Street, take increasingly bucolic turns to find a double-whammy of winery neighbors. Tastemaking Scribe Winery serves farm-to-table snacks and terroir explorations at its sublime hacienda, a 19th-century estate once left to ruin (and turkey farming), now an idyll in the breezes of the Petaluma Gap. Next door, Gundlach Bundschu Winery, the oldest continuously family-owned winery in California, provides a perfectly unfussy experience on lush, sprawling grounds. On Fremont Drive, sop it all up with a crucial second lunch at Lou's Luncheonette, a gourmet Southern roadside diner, before jumping back on the 12. 

Cross the Napa County line to find agrarian-chic Hudson Ranch and Vineyards: hikes through plus farmlands and wine picnics. Nearby, browse the di Rosa Center for Contemporary Art, a collection and sculpture garden featuring modern Northern Californian artists.

We land at Carneros Resort & Spa for a dose of choose-your-own-unwind, from booking a hilltop poolside cabana to a simple hangout by the fireplace at the outdoor pavilion for a post-road cocktail (your call). Live music. Bocce. All things good and true.

Wildsam Napa & Sonoma Guidebook Cover

Day 3: Exploring Olivet Road

On Olivet Road, four wineries offer diverse entry points into the world-class Russian River Valley grape-growing region.

Founded by fireman Cecil DeLoach in 1975, DeLoach Vineyards helped create the Russian River Valley American Viticultural Area, now one of the nation's brand-name wine territories. Pinots soar, as do dry riesling and beautiful gardens (and goats!).

At Harvest Moon, winemaker Randy Pitts is known for zins, but also makes beautiful dessert wines from late-harvest gewürztraminer. The down-home estate hits hospitality high notes while remaining amiable–a family- friendly, drinks-by-the-pool feel. Yes, the name is a Neil Young callout.

The grandson of Cecil DeLoach helms Hook & Ladder Winery, producing from estate-grown fruit. Go for the chardonnay, stay for the fire department memorabilia.

Iron Horse Vineyards, located on Ross Station Road about twelve minutes from Olivet, began as a pinot house but is now renowned for sparkling wines, served at the White House for six administrations. (Reagan and Gorbachev toasted with Iron Horse.) CEO Joy Sterling is a political activist and industry force and the hilltop tasting room is not to be missed. Finish the day with handmade pasta at Canneti Roadhouse in Forestville.

"Wine is just fruit," says Andrew Mariani, vintner at Sonoma County's acclaimed Scribe. "But it can give you this strange, mysterious feeling." The feeling definitely grows as one heads deeper into the lands of Napa and Sonoma, exploring these valleys ripe with history. It may start with the pursuit of wine, but the journey can be defined differently for everyone. 

Zach Dundas is an editor for Wildsam, where he's led the charge on books about the Grand Canyon, Seattle and—tough duty!—Napa and Sonoma. Based in Portland, he's the co-creator of the history podcast Death in the West and author of two books.