What was once a small farming community has morphed into one of California’s chicest wine country towns. Brimming with stylish boutiques, “it” restaurants, and more than two dozen tasting rooms, this gem in northern Sonoma County still retains much of its small-town charm.
Sip your way around Healdsburg’s leafy main square. Start at Cartograph Wines, specializing in Pinot Noir, as well as terrific dry Gewürztraminer and Riesling varietals. It’s a quick stroll to Banshee Wines, where you can enjoy its cool-climate Pinot Noir in a casual tasting room that features reclaimed-wood walls, distressed leather furniture, and cool music on vinyl. Finish out the day at Davis Family Vineyards, known for its Soul Patch Pinot Noir, along with Chardonnay and Rhône-style wines. While away the afternoon in the garden lounge, where you can nosh on cheese pairings and try your hand at bocce.