One of Healdsburg's oldest wineries, founded in 1876 by two Tuscan brothers who followed the Gold Rush west but found wine more reliable than gold. The original stone winery building is still standing, and the winery's aged redwood barrel room — built in 1890 — is a genuinely atmospheric place for a tasting. Simi focuses on Sonoma County Chardonnay, Cabernet Sauvignon and Sauvignon Blanc; the Alexander Valley Cabernet is consistently one of the area's better values.
The tasting room is open daily without appointment, making it an easier entry point into wine country than many of the smaller appointment-only operations in the area. The redwood tree outside the winery is the same age as the building.