Healdsburg Plaza forms the lively core of the town, surrounded by numerous wine tasting establishments. Laurel Livezey, the head sommelier at Little Saint, suggests beginning your wine journey at LIOCO, celebrated for its vibrant, minimally-processed wines from Sonoma's and Mendocino's cooler climates. Livezey specifically praises their Chardonnay. For more exceptional cool-climate wines, Ernest Vineyards offers tastings of their Sonoma Coast wines. Less than a mile from the plaza, Bacchus Landing hosts several other tasting rooms, including Dot Wine, which specializes in Russian River Valley Pinot Noir. SingleThread's owner-chef, Kyle Connaughton, enjoys visiting Marine Layer on his rare days off, appreciating its thoughtful approach to wine in a relaxed setting.
For those seeking an extraordinary dining experience, a reservation at the acclaimed SingleThread is a highlight, though often challenging to secure. As an excellent alternative, Troubadour, founded by former SingleThread staff Melissa Yanc and Sean McGaughey, presents a more accessible yet equally refined seven-course tasting menu inspired by French cuisine and utilizing fresh Sonoma produce.
Begin your Saturday with a visit to Quail & Condor, one of the nation's most celebrated bakeries, also established by the husband-and-wife duo behind Troubadour. Indulge in their famous sourdough-based avocado or lox toasts, or choose from an array of delectable croissants and pastries. Following breakfast, immerse yourself in the local flavors and artisan products at the Healdsburg Farmers’ Market, showcasing Sonoma County's rich agricultural diversity beyond vineyards. Livezey describes it as a small market, yet abundant with beautiful produce, flowers, and handcrafted goods.
Both Circe Sher, co-founder of Piazza Hospitality, and Laurel Livezey recommend a leisurely float down the Russian River by kayak or canoe, offering a peaceful and remote escape just moments from Healdsburg's bustling center. Local operators like Russian River Adventures and River’s Edge Kayak and Canoe provide self-guided trips. For lunch, Healdsburg's downtown offers diverse options. Alison Smith-Story of Smith Story Wine Cellars favors Little Saint for its plant-based brunch and curated chilled wine selection. Bravas Bar de Tapas has been a long-standing favorite for its traditional and modern Spanish tapas and sangrias since 2012. Troubadour also serves quick and casual sandwiches made with freshly baked bread.
Healdsburg's strategic location provides easy access to the Dry Creek Valley AVA and Alexander Valley AVA. Kyle Connaughton highly recommends Reeve Wines in Dry Creek Valley for its relaxed atmosphere, expressive wines, and seasonal pies from their wood-fired pizza oven. In Alexander Valley, Jordan Winery offers tastings of its Cabernet Sauvignon and Chardonnay in a private setting, complemented by gourmet bites crafted by chef Jesse Mallgren.
For an evening break from wine, head to Lo & Behold Bar + Kitchen, a popular industry spot known for its eclectic comfort food and innovative cocktails. Their menu, including the fan-favorite kimchi noodles, changes seasonally. While wine tasting rooms close earlier, Healdsburg's wine bars offer late-night options. Alison Smith-Story suggests Maison Healdsburg for a nightcap, praising its extensive selection of Italian, Californian, and European wines available until 1 a.m.
On Sunday morning, if you're seeking a hearty breakfast, Acorn Cafe is an excellent choice, offering satisfying dishes like huevos ranchero or a breakfast sandwich. Before heading to the airports, a stop at Aperture Cellars provides a change of pace with Bordeaux-style wines and breathtaking views. Kyle Connaughton admires Aperture for its seamless blend of architecture, art, and exceptional winemaking. Finally, J Vineyards & Winery specializes in traditional method sparkling wines, best enjoyed with their five-course pairing menu in the Bubble Room, featuring locally sourced ingredients that change seasonally.
Staying in downtown Healdsburg ensures convenient access to tasting rooms, restaurants, and shops. Piazza Hospitality manages three minimalist, art-centric hotels within walking distance of each other and the downtown area. Hotel Healdsburg offers a traditional luxury experience with a spa and multiple dining venues, including Charlie Palmer’s Dry Creek Kitchen. H2 Hotel caters to a younger demographic with its eclectic design and solar-heated creekside pool. Harmon Guest House provides a cozier, more residential ambiance. For a lavish experience, The Madrona, housed in a 19th-century Victorian mansion, features uniquely decorated rooms and curated artwork, recognized as one of Sonoma’s top hotels.