With boundless charm and that irresistible only-in-California beauty, Healdsburg, a small city in Sonoma County, is a must-visit destination in the state’s wine growing region. In 2024, it was named one of the “Best Cities in the Country” by Condé Nast Traveler, and for good reason. It not only boasts an elevated small-town vibe sans the pretentiousness of other nearby cities, but it is nestled along the banks of the Russian River and the gateway to three famous winegrowing regions, the Russian River Valley, Dry Creek Valley, and Alexander Valley.
From winemakers to farmers, artists, and entrepreneurs, the hills of Healdsburg are brimming with talented women-owned businesses and leaders that make up the fabric of the city.
Where to eat
Little Saint
Little Saint is a coffee bar, lounge, music venue, and restaurant that is always buzzing with activity. In addition to great wine from local labels, including Ernest Vineyards, Dot Wines, Sutro Wines, Poralupi Wines, and Smith Story Wine Cellars, each founded or co-founded by women, diners get a taste of its vegetarian food while supporting many causes the restaurant endorses including sustainability, climate justice, and animal welfare.
Lo & Behold Bar and Kitchen
Hospitality veterans Laura Sanfilippo and Tara Heffernon decided to open a restaurant that would bring in locals and be a hangout for industry professionals. Lo & Behold has a robust menu of signature cocktails and crowd favorite comfort food, including Coconut Shrimp Toast, housemade Kimchi Noodles, and Almost Famous Chicken Tendies.
Troubador Bread & Bistro
A visit to Healdsburg isn’t complete without dining at one of Melissa Yanc and Sean McGaughey’s restaurants Michelin recognized Quail & Condor and Troubadour, a James Beard semi-finalist. Troubadour serves artisan bread and local favorites by day. By night, it transitions to an intimate setting, offering a seven-course tasting menu showcasing Sonoma’s finest ingredients, sourced from producers the chefs know personally.
Where to sip
J Vineyards and Winery
For a dazzling wine and cheese tasting experience, visit J Vineyards & Winery. Head winemaker Nicole Hitchcock crafts sparkling and varietal wines grown in the Russian River Valley. The Legacy Room’s tasting room views, decor, and delicious wines make it an essential part of any wine tasting itinerary.
Jordan Vineyard & Winery
Nestled on a 1,200-acre estate in Alexander Valley, a visit to Jordan Winery is like a journey to a French chateau complete with panoramic vistas, beautiful art, and delicious pairings. Head winemaker Maggie Kruse and her team oversee operations and has helped make the brand a top producer of Cabernet Sauvignon and Russian River Valley Chardonnay.
Where to play
Single Thread Farms
The 24-acre farm, home to more than 300 varieties of crops, provides tours showcasing edible flowers, garnishes, fruits, and vegetables used at Sonoma County’s only three-star Michelin restaurant. Visitors can explore the farm through 1.5-hour guided walks, participate in flower arranging classes, and shop in the farm store.
Healdsburg Plaza
While wine might flow through Healdsburg, its plaza is at the heart of the city. Shops, restaurants, and more than two dozen art galleries line the streets near the hub, making it a central stop for the best finds. Bon Ton Studio features a carefully curated selection of the season’s fashions, while Falling for Dainty, a contemporary jewelry brand, showcases permanent jewelry and handmade pieces. La Ruche is one of the plaza’s newest tenants and boasts a French-inspired outpost full of honey from across the globe. Owner Nicole White proffers the best honey and bee-infused educational tidbits for her guests.
Where to stay
Hotel Healdsburg
Centered off the main square and steps away from the best of what the city has to offer, Hotel Healdsburg provides luxe accommodations, an onsite spa, a swimming pool, and an award-winning restaurant. Owned by Plaza Hospitality and managed by visionary hotelier Circe Sher, Hotel Healdsburg, “the living room of the community,” has two sister properties, Harmon Guest House and h2Hotel, each with unique accommodations with art and sustainability at the forefront of their design.
Grape Leaf Inn
Delicious food and history go hand-in-hand in the quaint bed-and-breakfast Grape Leaf Inn. Co-owned by Diane Wilson of Wilson Artisan Wineries, the 13-room house features a temperature-controlled pool and a seasonal and sustainable menu that changes daily based on availability. Don’t miss the hidden library door that leads down to a speak-easy for private events or dinners.