Healdsburg is a small Sonoma County town of about 11,000 people, sitting at the confluence of three premier wine-growing valleys: Alexander, Dry Creek, and Russian River. It's an easy two-hour drive from San Francisco and draws visitors primarily for its wineries, though the tree-lined central plaza — lined with restaurants, tasting rooms, and coffee shops — is genuinely pleasant to spend an afternoon in.
The surrounding valleys are beautiful, with rolling vineyards, redwood groves along the river, and quiet back roads ideal for cycling. Dry Creek Valley is known for Zinfandel; Russian River Valley produces excellent Pinot Noir and Chardonnay; Alexander Valley runs warmer and suits Cabernet Sauvignon. Most wineries are small, appointment-preferred operations rather than big commercial affairs.