1. Where to Stay
Unwind in a soaking tub overlooking Foss Creek at h2hotel, a green-minded, month-old spot whose earth-tone rooms are decked with bamboo floors and sustainable wood furniture (from $215). Stop by the front desk before breakfast to rent one of the seven complimentary Euro-style Public cruisers, available on a first-come basis starting at sunrise.
Lounge among the gas fireplace, grand four-poster bed, and nineteenth-century European antiques at the decadent Les Mars, a sixteen-room boutique hotel that evokes a classic French B&B (from $575). The European- and Asian-inspired restaurant, Cyrus, boasts a Michelin star.
Check out sunbathers from your bungalow’s pool-front patio at Duchamp Hotel, a fashionably minimalist estate with concrete floors and spare white walls (from $350). Enjoy breakfast in the courtyard beneath the hotel’s shady olive grove.
2. Where to Eat
Choose from 650 Sonoma-made wines at chef Charlie Palmer’s Dry Creek Kitchen. The restaurant’s Sonoma Neighbor Menu features fish, meat, and produce from nearby farms like Early Bird Farms and Gleason Ranch. Arrive at 5:30 p.m. on weekends to secure a seat on the outdoor patio.
Order a round of thin-crust pizzas—cooked in a 650-degree wood-burning oven—and specialty cocktails made from freshly squeezed fruit at Medlock Ames’s two-month-old wine bar and tasting room. The fresh herbs and spices garnishing cocktails and pizzas are grown in the back garden.
Call a week in advance to reserve a spot at former Dry Creek chef Mateo Granados’s thrice-weekly Tendejon de la Calle (“taste of the street”) pop-up dinners, set in a vineyard warehouse and capped at 40 diners a night. The Yucatán-inspired menu changes each week and the wine is BYO (707-623-5474).
Pair local cheeses with wine cocktails at the Speakeasy Wine Club, a four-month-old tasting room hidden in the back of a wine shop (step into the phone booth, PDT-style, to enter). Over two dozen vintages are available by the glass, with a particular focus on Russian River–region varietals.
3. What to Do
Call ahead for a personal tour of boutique winery Captûre, a mountain estate overlooking the Alexander Valley that touts some of the highest-elevation vines in America. The spot is helmed by venerable third-generation winemaker Denis Malbec, who oversaw Bordeaux’s Château Latour before decamping to California in the early aughts. Now releasing its second vintage, the winery is particularly known for its bold, Bordeaux-style Cabernets.
Browse vintage pop-art paintings by Stanley Mouse at Rockin Roses Gallery, opened in June 2010. Mouse made a name for himself designing concert posters and record covers for Journey, Janis Joplin, Hendrix, and the Grateful Dead during the psychedelic seventies. Here, he sells rare works like an original Hendrix design for $250,000 and the original artwork to his iconic “Zig-Zag” poster—an ad for Zig-Zag rolling papers—for $1 million. Numbered and signed paintings on LSD blotter paper are $300.
Stroll through Long Meadow Ranch’s fragrant herb, flower, and vegetable gardens in nearby St. Helena (open 11 a.m. to 6 p.m.). In addition to vineyards, the 5.8-acre property produces grass-fed beef, eggs, olive oil, honey, and produce, all sold in the on-site market. Afterward, sample wines—particularly the 2005 Cabernet Sauvignon—and fresh-pressed olive oil at the renovated five-month-old tasting room.
Listen to local jazz and bluegrass bands like the Mountain River Valley Boys at the Healdsburg Farmers Market (Saturdays though November, 9 a.m. to noon). The 32-year-old market draws farmers, flower growers, dairy men, fishermen, bakers, butchers, tamale-makers, and more—most from within a ten-mile radius.
4. Insider’s Tip
Of over 100 wineries spanning the Healdsburg region, Preston Vineyards is one of the few that caters to families. In addition to the tasting room—try the Guadagni Red, a traditional jug wine blend of Zinfandel, Mourvèdre, and Carignane—the estate includes apple and olive orchards, an organic farm, and a sizable picnic lawn with views of the scenic Dry Creek Valley hills.
5. Oddball Day
Spend a day floating down the Russian River, which runs through Healdsburg before emptying into the Pacific 60 miles north of San Francisco. Start at Flying Goat Coffee, a fragrant African and Latin American bean emporium known for its made-to-order French-press coffee. Stop off at Cheese Shop (423 Center Street; 707-433-4998) and pack a picnic lunch of local cheese, bread, and charcuterie. Then, make the five-minute drive to Russian River Adventures, which provides sturdy, inflatable canoes for daylong rafting trips ($49 for adults; $24 for kids). Though the river turns choppy in the winter, the flow is meandering through the end of October. The 8.5-mile, five-hour trip runs from Healdsburg Memorial Beach to the town of Forestville, winding past nesting herons, egrets, and verdant vineyards. Stop at one of the sandy beaches along the bank to unpack your lunch and sway from the low-hanging rope swings. Afterward, take a half-hour drive to Calistoga’s Petrified Forest, a 3 million-year-old redwood forest dotted with wildflowers. The half-mile main trail offers views of Mount St. Helena, spanning Sonoma and Napa Counties. Finally, head back to Healdsburg for green-chile-topped burgers and microbrews at Bear Republic Brewery.
Inside Sonoma is local wine and entertainment site with a dose of snark.
Healdsburg Wineries is an easy-to-follow guide to Healdsburg’s best winemakers.
Sonoma Uncorked offers reports on the region’s food scene.
Sonoma County Vintners details winery tours and tasting routes.