The Perfect Three-Day Weekend in Sonoma

Just 40 miles north of San Francisco lies the underrated enclave of Sonoma—a vineyard-strewn swath of land that spans from the edge of Napa to the Pacific Ocean. In Healdsburg, wine country dining is at its peak, and as you work your way west along the Russian River, you’ll find plenty of laid-back wineries pouring impressive Pinots and sparkling wines. Without the Napa crowds or San Francisco fog, it’s a prime place for a long weekend of wine tasting, river swims, and exploring the coast. You’ll want a car to get the most of the area's attractions, so rent one and head north on Highway 101. Here’s what to do when you arrive to maximize your weekend vacation in Sonoma.

Day One

Ease into Sonoma’s slow-paced lifestyle in Healdsburg, a walkable 19th-century town that is quickly becoming a hub for upscale wine-country fare. Lunch at the Shed is a crash course in the bounty of Sonoma’s ingredients. The restaur also displays the region’s experimental ethos, as evidenced by their workshops, supper parties, and fermentation bar. Hold out for dessert at Noble Folk, where fruit-filled pies and palate-bending ice creams (think strawberry-sage) are the only things on the menu. A few blocks away is Seghesio Family Vineyards, which has produced the region’s famed zinfandel since 1895. The estate is a stone’s throw from downtown, and has a bocce court, shaded picnic grove, and tasting room featuring flights and food and wine pairings. Bed down at Hotel Healdsburg, a central modern inn with a relaxed pool and spa.

Day Two

Start your second day by heading west on the aptly named River Road, a scenic forested road that traces the Russian River flowing through the county, all the way to the Pacific. Along the way are mellow wineries, like La Crema’s brand new estate tasting room featuring a chic multi-level barn and picnics paired with their Sonoma Coast Pinot Noirs. Break in Guerneville, a tiny former logging town that is gaining momentum as a destination for quaint places to eat and craft beer on the shores of the Russian River. Bust out your bathing suit for a dip in redwood-lined river, then head to town for oysters and uni at the trendy Seaside Metal raw bar. Head to El Barrio Tequila Bar for a nightcap, then turn in at the new Autocamp “glampground” featuring tricked-out Airstream trailers and fire pits.

Day Three

Head toward the coast on your third and final day. A short drive west of Guerneville, the craggy Sonoma coastline attracts people for what it lacks (crowds, tour buses, cell phone reception) as much as what is (seabirds, shell-strewn beaches, views for days). The blink-and-miss-it town of Jenner sits at the intersection of where the Russian River meets the ocean, and is a good basecamp for renting kayaks or standup paddleboards from WaterTreks EcoTours to explore the estuary. A few miles up Highway 1 is the reinvented Timber Cove, perched on 25 acres of rugged coastline with trails, fire pits, and VIP views. The Frank Lloyd Wright-inspired A-frame structure is a must-see for any design buff. And the seafood-focused menu at the property’s new restaurant, Coast Kitchen, is one of the most inspired on the North Coast.

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