Healdsburg is the Goldilocks of Wine Country.
Quainter than Napa and ritzier than Sonoma, it has that perfect balance of luxury and small town charm we crave when visiting the rolling vineyards of Northern California. It’s no wonder the city has evolved rapidly over the past decade, from a sleepy farming community into what is arguably Wine Country’s hottest destination of the moment.
A little more than an hour north of San Francisco, Healdsburg makes an ideal day trip from most of the Bay Area. If you can shell out some coin, it’s terrific for a weekend escape. Yes, a trip here can mean Michelin stars, pricey bottles of wine, and wildly expensive overnight stays—but it doesn't have to. There are plenty of more laidback options, too.
From great restaurants and delightful stays to sprawling vineyards and charming tasting rooms, our modern guide to Healdsburg will steer you right.
The Best Restaurants in Healdsburg
Spanish tapas at Bravas Bar
(Courtesy of @bravasbardetapas)
Higher-End Restaurants
It didn't take long for SingleThread (31 North St.) to make an impression. In 2018, the restaurant became the first Sonoma County restaurant to receive three Michelin Stars, and it did so in just its second year. The vibrant 11-course tasting menu employs techniques and philosophies inspired by founders Kyle and Katina Connaughton’s time living in Japan, and features ingredients grown on the couple’s nearby 24-acre farm. The on-site inn is also a luxurious treat: You can order in-room dining and a restaurant reservation is guaranteed. // The tri-level Matheson (106 Matheson St.) became an instant classic when it opened in late 2021 directly across from the town plaza. On the first floor, you’ll find a state-of the-art wine wall and the upscale restaurant led by chef and owner Dustin Valette and featuring local farmers, fishermen, and purveyors. More casual fun happens upstairs with wood-oven pizzas and vibrant seasonal cocktails in the rooftop lounge. // Barndiva (231 Center St.) is a special occasion spot that's simultaneously elegant and rustic. The atmosphere screams Wine Country, with farm animal–themed artwork, antique fixtures, and a tree-covered gravel patio draped with twinkle lights that's positively hopping on weekend nights. As for the food, it's fresh, sophisticated, and beyond tasty. If you can't swing dinner, opt for an epic brunch. // Ten minutes from Healdsburg is chef Douglas Keane's Michelin-starred Cyrus (275 CA-128). For $325 per person, guests live it up with 20 courses in a series of different rooms throughout the evening. After starting with canapes and cocktails, diners progress to small bites at the kitchen table and larger entrees in the dining room overlooking the vineyards. Dessert is a true finale.More Casual Eats + Treats
Debuted in 2022, the ambitious 10,000-square-foot Little Saint (25 North St.) is a community gathering space with a coffee bar, a cafe and bakery, a wine lounge, a restaurant serving 100-percent plant-based cuisine, music venue, and Ken Fulk-designed stay. Wines are sourced from wineries committed to responsible farming with a focus on BIPOC and women winemakers. Look out for weekly live music, book signings, film screenings, and more. // With its wood-oven pizzas and hearty pastas, Pizzando (301 Healdsburg Ave.), perched on the corner of Healdsburg’s main square, is a refreshing departure in a town full of small plates. Choose a spot inside the newly renovated dining room or the sidewalk parklet that’s perfect for people-watching, and order antipasti, Neapolitan- and Roman-style pies, focaccia, and grilled meats. // Sweet little Noble Folk Ice Cream & Pie Bar (116 Matheson St.) on the square taps into the hipster in all of us with the likes of "heritage pies" (such as the amazing chocolate maple walnut), as well as scoops of ice cream the size of your head in flavors like pistachio cherry, almond matcha, and vegan passion fruit. // With perhaps the best patio in town, traditional Spanish restaurant Bravas Bar de Tapas (420 Center St.) is brought to you by beloved Sonoma County restaurateurs and James Beard finalists Mark and Terri Stark. Bravas is lively—note the list of gin and tonics at the outdoor bar, where they broadcast the local games—and solid for shareable plates such as duck meatball bocadillos and crispy pig ears. // Sunny little Parish Café (60 Mill St.) on the way into town from the 101 (take the Central Healdsburg exit) is a slice of the South plopped in Wine Country that's perfect for a quick breakfast or lunch before wine tasting. Pick from your poison of po'boys, share an order of fried pickles, and don't miss the beignets. // Healdsburg’s favorite bakery Quail & Condor (44 Mill St., Unit J) recently went from a tiny space to 3,650 square feet with plenty of room for seating and enough staff to significantly speed up its notoriously long lines. Order off the cafe menu for Turkish-inspired simit and quiche, but don’t miss sweet and savory pastries and breads including kouign amann and parmesan onion biscuits.
Healdsburg's Best Wine Tasting
Jordan Winery
(Courtesy of Jordan Vineyard & Winery)
Vineyards + Wineries
Nestled in the middle of some of California's top wine regions—Russian River, Alexander Valley, and Dry Creek Valley—Healdsburg is a prime wine tasting destination that many people skip in favor of Napa and Sonoma. Big mistake.
A large part of the region has made its name on producing top notch, cool-climate chardonnay and pinot noir. Family-owned Arista Winery (7015 Westside Rd) is a fantastic representation of this region's prowess, for they cut no corners when it comes to the quality of their wines. // We love MacRostie Winery (4605 Westside Rd), not just for their pinot and chard, but their gorgeous digs and panoramic views of the Russian River Valley. // Limerick Lane (1023 Limerick Ln.), a humble century-old winery, offers zinfandel and Rhone varietals, in addition to pinot and chard in a refreshingly unpretentious atmosphere with stunning views. // The historic Seghesio Family Vineyards (700 Grove St.) has been making wine in Healdsburg for over 120 years and is one of the few California wineries that managed to survive Prohibition. This Italian family is known for their zinfandel and Italian varietals. // At Jordan Vineyard & Winery (1474 Alexander Valley Rd.), a stunning ivy-clad chateau, you can visit the massive chef's gardens on a tours across the 1,200-acre estate. For an incredibly special day at a winery with a female winemaker at the helm, head to Sutro Wine Co. (13301 Chalk Hill Rd.), which specializes in minimal intervention, small-scale production of volcanic terroir wines. The signature tasting experience is truly soil to glass: Guests start with a 45-minute hike throughout the ranch before a relaxing tasting in a shaded oak grove or, if the weather is less than ideal, in a modern tasting room nearby on the estate. // On more than 1,300 acres, Chalk Hill Estate (10300 Chalk Hill Rd.) is known for its sweeping vistas, sustainable farming practices, and curated tastings like guided horseback riding tours through the vineyards. // Sparkling wine lovers should head to J Vineyards (11447 Old Redwood Hwy.), where the J Bubble Room hosts a multi-course, sit-down lunch paired with still and sparkling wines. // Set in an Italianate villa and surrounded by blooming gardens, Ferrari-Carano (8761 Dry Creek Rd.) has been producing award-winning wines for more than 40 years. A leader in sustainability, the winery also has several tasting and food experiences, including in the underground Enoteca.
Wine Tasting in Healdsburg's Main Square
Don't have a designated driver? Another great aspect of Healdsburg is the ability to try several wineries without a car. Take a walking wine tour around the main square, stopping by some of our favorites, like Siduri (235 Healdsburg Ave), whose pinots span California and Oregon. // Marietta Cellars (250 Center St.) is best known for their iconic Old Vine Red blend, but that's not the only thing offered at their new, contemporary tasting room downtown. It's also the place to find their Etta Series: light, fresh, small-lot wines that break the mold. // Another newcomer to the square is the first tasting room from beloved natural wine purveyor, Martha Stoumen (325 Center St.). The warm, friendly space with vintage accents is a nice fit for the playful 12-year-old label specializing in more esoteric Italian varietals.
Where to Get Cocktails, Coffee + Tea in Healdsburg
Cocktails at Spoonbar
(Courtesy of @spoonbarhealdsburg)
Come to Spoonbar (219 Healdsburg Ave.( on balmy evenings when they open the retractable walls or grab a seat on the expansive back patio to indulge in market-driven craft cocktails. Seafood Sundays and fried chicken Wednesdays are also good nights to stop by. // Duke's Spirited Cocktails (4113, 111 Plaza St.) is carrying on a long tradition of slinging drinks to Healdsburg residents in a location that dates back to 1933. A true local watering hole, Duke's serves original cocktails with locally made spirits and home-grown ingredients. // Sip sake cocktails or take a break from the booze with a Marteani (get it?) at Taste of Tea (109 North St.). The menu also features nine kinds of matcha, tea lattes, and scientific siphon pot infusions. Pair your beverage with ramen, rice and noodle bowls, or other Japanese bites. Stay for a treatment at the in-house tea spa, offering Japanese green tea–infused R&R. // Third wavers, Flying Goat (300 and 419 Center St.)is your haven for coffee. Their ethically sourced beans and quality roasts of have won awards for years, plus they have yummy pastries on-hand for quick stops. There are two locations, so if one is packed, try the other. // Located along the main square, Black Oak Coffee (324 Center St.) is spacious and cozy with comfortable seating and fast WiFi. The basic drip coffee is excellent, as are the more gussied-up options such as the lavender latte, black oak nitro cold brew, or sweet dirty chai oat milk latte.
Where to Stay in Healdsburg
A guestroom at Liora Estate
(Courtesy of Liora Estate)
Located mere steps from the historic town plaza, Hotel Healdsburg’s prime location (25 Matheson St.) is one of the stay's biggest perks, along with modern guest rooms, a luxurious spa, 60-foot pool, and acclaimed onsite restaurant, Dry Creek Kitchen. // With its eclectic decor and stunning transformation from historic mansion to posh boutique inn, The Madrona (1001 Westside Rd.) has been named one of the hottest new hotels in the country by Condé Nast Traveler. The 24-room hotel features 250 pieces of the art and furniture original to the home, paired with luxurious new trappings for a warm and stylish vibe. // If you want to be close to the action but feel far away, Montage Healdsburg (100 Montage Way) is the Forbes five-star resort—situated among oak tree groves and vine-covered hills a few miles north of the square—of your luxury-loving dreams. The 130 modern bungalow-style guest rooms and suites have been eco-consciously designed with their own outdoor oases. World-class amenities include treatments at the expansive 11,000-square-foot spa, a zero-edge swimming pool, and decadent meals at three on-site restaurants. // From the same developers behind the eco-chic Hotel Healdsburg and H2Hotel, Harmon Guest House (227 Healdsburg Ave.) is a geometric and modern design masterpiece, as well as a sustainability super star with natural light and a bevy of amenities: free cruiser rentals, a solar-heated pool, complimentary Sunday yoga, daily breakfast, and a rooftop in town with a fire pit, bar, and panoramic views. // Hotel Trio, a Marriott property (110 Dry Creek Rd.), is a more budget-friendly option where stays include a complimentary breakfast buffet, two-hour free bike rental, pool and fitness center, and a lobby bar that features local wine and beer. Need something delivered to your room? On-site robot concierge Rosé the Robot will bring it to you in a hurry. As Healdsburg's only all-suite hotel with full kitchens, it is also a great choice for families and large groups. // Opened last year, Appellation Healdsburg (101 Dovetail Ln.) from celebrity chef Charlie Palmer is luxury without the pretention. Set on 8.5 acres right outside of downtown, the flagship property for the culinary-forward brand is state-of-the-art with, no surprise, an excellent signature restaurant, Folia Bar & Kitchen and sexy rooftop bar. // Just opened Liora Estate (27 North St.) is a newly reimagined 16-room, European-inspired boutique hotel right off of the plaza. Centered on connection and slow luxury, the property is woven through with daily rituals like wine hours, candlelit evenings, elevated coffee experiences, and record-spinning gatherings in the library lounge.
Where to Shop in Healdsburg
A curated selection of goods at Forager
(Courtesy of @foragerhealdsburg)
The easily walkable Healdsburg square is lined with independent shops. Head to Bon Ton Studio (120 Matheson St.), a carefully curated boutique, for classic wardrobe staples, woven fabrics, and various decor. Its sister store, Bon Ton Baby, has the same aesthetic but for kids. // Find festival-worthy attire at Gathered (322 Center St.). // Punch (387 Healdsburg Ave.) is well-stocked with quality trendy pieces for women. // Anthem (118 Matheson St.) has two-levels of upscale homegoods, including linens and luxury furnishings. // At Forager (310 Center St.), you'll find a curated selection of beautiful items for the kitchen, tabletop, and more. // For Italian food provisions and biodynamic wines, check out Ciao Bruto! (130 Plaza St.). // Lucky Heron (333 Healdsburg Ave.) offers an eclectic assortment of creative gifts. // Jam Jar (126 North St.) features original art, handcrafted jewelry, and housewares.
