Where to Sip and Stay in Northern California’s Wine Country

In a previous career, I traveled from New York to San Francisco a few times per year to meet with tech bigwigs. One fine, foggy evening in SF—not the chill to the winter but a nip to the air—I trudged up hilly streets to Zeki’s, a top-notch dive in Nob Hill. A draught of Anchor Steam in hand and an old Grateful Dead number on the jukebox, I met a woman at the bar named Scarlet Begonias, a California beauty with rings on her fingers and bells on her shoes. She was into the blues. By the time Zeki’s closed—many rounds of Anchor Steam later—I had already canceled my flight back east to sweep her off her jingling feet in the most romantic refuge I knew: Wine Country. 

My Cali queen would later elope with the leader of a free-love commune outside Big Sur. But my love affair with the Wine Country proved more enduring, and I return to that august corner of NorCal every chance I get. Beyond picturesque vineyards and exquisite vintages, Wine Country promises a feast of delights—the world-class restaurants and boutique hotels of Napa; the laid-back, rustic charm of Sonoma; the verdant, mist-shrouded mountains of Mendocino further north. It’s a slice of heaven just north of San Francisco. 

For a full pour of Wine Country magic, take a road trip through Sonoma, Napa, and Mendocino counties. Although close together geographically, each of these viticultural meccas differs in topography, wine styles, and personality. You can explore all three counties with a set of wheels and 4-5 days. The cities of Sonoma and Napa are just half an hour from one another, while Mendocino and its neighboring towns are a couple hours drive north. Below are my favorite places in each region to dine, wine, and unwind.

With rolling emerald hills, lush farmland, and sleepy roads, Sonoma County is like a Californian take on Tolkien’s Shire. In addition to its county seat, the region is home to storied winemakers in quaint towns like Healdsburg, Glen Ellen, and Geyserville. Oenophiles the world over covet Sonoma’s elegant Pinot Noir, Zinfandel, and Chardonnay, and the mild Mediterranean climate likewise nourishes exceptional olives, apples, and stone fruits. Before its rise as a viticultural powerhouse, Sonoma was ranching country, and hints of its cowboy heritage are still palpable.

Named after the Latin word for “gift,” The Donum Estate in the city of Sonoma began as a passion project to craft the world’s finest Pinot Noir—a notoriously challenging grape that, when grown successfully, yields wines as perfumed as ambrosia (cue the Paul Giamatti Sideways monologue). Donum’s proprietors are art connoisseurs, and sculptures by luminaries such as Ai Weiwei, Yayoi Kusama, and Keith Haring adorn the property’s hillocks and vines. Look closely at the label of the bottles—the playful illustrations are by Ai Weiwei.

All Donum Estate’s wines are Regenerative Organic Certified, a rigorous designation bestowed on farms that eschew pesticides, prioritize soil health, and engage in community improvement initiatives. Regenerative organic agriculture is a boon for the environment and your palate, translating to wines that vividly express terroir. Each pour of Donum is like the essence of Carneros, the American Viticultural Area (AVA) within Sonoma, captured in a glass. The pristine estate is also a haven for birds like blue-tailed herons, eagles, and California scrub-jays. 

Book an appointment online to visit Donum’s tasting room, a high-ceilinged salon overlooking the vineyards. The Culinary Experience includes wine tastings and a gourmet lunch—the kind of seasonal, locavore fare that would make Alice Waters smile from above. For a guided tasting followed by a tour of the vineyards and sculpture collection, book the Explore Experience.

Troubadour Bistro in Healdsburg is an institution for coffee in the morning and fine dining in the evening. The seven-course tasting menu flows with the seasons and showcases the bounty of Sonoma prepared with French finesse. The night I dined at Troubadour Bistro, highlights included escargot braised in red wine, roasted duck breast with morel mushrooms, and a parade of wines that gorgeously complemented each plate. 

For a worthy splurge, book a table at SingleThread, a three-Michelin-star restaurant in downtown Healdsburg helmed by chef Kyle Connaughton and his wife Katina. The 11-course tasting menu—a paean to Sonoma county’s farms, forests, and waters—nods to Japanese kaiseki, a series of artfully presented small plates. The service exemplifies omotenashi, the meticulous attention to detail characteristic of Japanese hospitality. The menu’s heirloom vegetables, herbs, fruits, and flowers come from the Connaughtons’ farm in Sonoma.

Perched atop a small mountain, Montage Healdsburg lodges guests in handsome cottages abutting the property’s vineyards. Espresso machines, spacious bathtubs, and indoor and outdoor showers grace each cottage. At dusk, turn on the balcony’s fire pit, don a blanket, and uncork a bottle to toast the sunset over the mountains. If you need something harder than wine, the al fresco lobby bar houses a splendid whiskey library. The hotel has a gym and a renowned spa—sound remedies for counterbalancing Sonoma’s rich indulgences. 

Like Nantucket, Aspen, and Jupiter Island, Napa Valley is synonymous with wealth and refined joie de vivre. Soaked in soft sunshine and framed by mountains, Napa is an epicurean garden where celebrated chefs and vintners ply their craft. It’s also home to several charming, well-heeled towns you’ve probably stumbled across on the back of a few choice bottles: like St. Helena, Rutherford, Yountville, and Oakville.  (Pro-tip: for a fail-proof way to broadcast baller status in a fancy restaurant, order a Napa heavy hitter like Stag’s Leap or Heitz Cellar.)

The first wine that ever blew my mind was a bottle of Château Margaux at Delmonico’s in New York City. Since that night, Bordeaux-style wines have been the darling of my palate. Napa has a similar climate and terroir to the storied French province, and Brasswood Vineyard in St. Helena cultivates Cabernet Sauvignon, Cabernet Franc, and Petit Verdot with all the painstaking care of the ancient monks of the Garonne Valley. With a slight incline and northeast exposure, the grapes ripen slowly, lending complex aromatics and graceful tannins.

Relish il dolce far niente—Italian for “the sweetness of doing nothing”—at Far Niente Winery in Oakville, one of Napa’s most iconic producers. Far Niente specializes in Cabernet Sauvignon and Chardonnay, and both expressions are magisterial. I am partial to robust, jammy reds, and Far Niente’s Cab is an orgy of strawberries, plums, and blackberries as fragrant as a summer market in Sicily. As in Bordeaux’s timeworn wineries, Far Niente’s cellars are carved into hillsides—cool, softly lit, natural caverns with tables for tastings. 

Anthony Bourdain had been around the block when it came to international super restaurants, but when pressed in an interview, he declared that the finest restaurant in the world was The French Laundry in Yountville. Helmed by Chef Thomas Keller, a giant in American gastronomy, the French Laundry is a bucket-list restaurant for serious gastronomes. Dinner at the French Laundry is for the gourmand what Pantera backstage passes are for the metalhead. 

The menu changes often, but classics like Oysters and Pearls, butter-poached mollusks and caviar set in a warm tapioca sabayon, and Coffee and Doughnuts, cappuccino semifreddo with a cinnamon-sugar doughnut, remain permanent staples. Reservations are difficult to snag, so book them as early as possible. Once inside the temple, plan to linger—dinner typically stretches over four hours.

Gaze at the manicured rows of vines of Beringer Vineyards from your suite at Alila Napa Valley, both in St. Helena. The hotel epitomizes Napa Valley’s refined opulence, with fireplaces, wraparound balconies, and Italian linens in each room. In the 19th century, waves of Italians immigrated to northern California, drawn by the Gold Rush and agricultural work. The menu at Violetto, Alila’s signature restaurant, pays homage to this diaspora, crafting Italian soul food with the gifts of Napa’s soil. In a region that’s not particularly pedestrian friendly, downtown St. Helena, brimming with boutiques, cafes, and tasting rooms, is just a short stroll from the hotel.

In my dissolute youth, I worked in Mendocino for a season, trimming buds for quick cash to backpack through Asia. I’ll never forget the majesty of the countryside—hills as rugged as the Scottish Highlands, dramatic ocean cliffs, and the first light of dawn slicing through the sea mist. Napa and Sonoma often overshadow Mendocino for wine, but Mendo is a hidden gem, where grapes kissed by Pacific zephyrs thrive at high elevations.

The owners of Bonterra Organic Vineyards, located between Healdsburg and the Mendocino coast, realized that root vegetables and leafy greens tasted better when grown in untainted soil, and they applied this minimal-intervention approach to viticulture. As with Donum, Bonterra is Regenerative Organic Certified, with vintners grazing sheep in between the trellises to manage cover crops. The wines are odes to Mendocino’s rains, soil, and winds. The Cabernet Sauvignon sparkles with notes of blackcurrant, black cherry, and prune, while the Pinot Noir is as redolent of crushed flowers and petrichor as the shawl of a Grecian forest nymph. The property itself is a veritable Eden of wildflowers, gurgling creeks, and Italian cypress trees.

The Harbor House Inn is a small hotel and restaurant, secluded on a sea cliff on the Pacific Coast Highway in the small town of Elk. Harbor House’s restaurant, run by chef Matthew Kammerer, boasts two Michelin Stars and a Green Star for sustainability. The menu is a hymn to the Pacific, with dainties like sake-poached abalone, sourdough bread sprinkled with sea lettuce, and West Coast uni. If you choose to stay the night after a seafood- and wine-laden feast, Harbor House offers luxury cottages with ocean views and access to a private cove. 

Nuzzled between Mendocino’s craggy coast and the redwood forest in Fort Bragg, The Inn at Newport Ranch is a working cattle farm with a bed-and-breakfast. The decor of each guest room is bespoke, and all rooms come with private decks, fireplaces, and breathtaking views. At night, ascend to the rooftop hot tub to sip wine, listen to the crashing waves, and gaze at the stars. The delicious seafood in Newport Ranch’s restaurant aptly complements the hotel’s cozy guest rooms.