Healdsburg's position at the northern end of Sonoma County puts it within easy reach of some excellent destinations by car.
Guerneville and the Russian River coast (45 min): Follow the Russian River southwest on River Road or Westside Road through the redwoods to Guerneville — a laid-back river town with good swimming holes, kayak rentals, and a distinctly different atmosphere from Healdsburg's wine-country polish. From Guerneville, the road continues another 30 minutes to Bodega Bay and the Sonoma Coast, with its dramatic headlands and beaches.
Mendocino (2 hours): The drive north on US-101 to Cloverdale, then west on Highway 128 through Anderson Valley, is one of the more scenic in Northern California. Anderson Valley itself is worth stopping in — a cool, foggy appellation producing excellent Pinot Noir and sparkling wine. The town of Mendocino sits on a headland above the Pacific; Portuguese-settled in the 19th century, it retains a Victorian downtown unlike any other on the California coast.
Point Reyes National Seashore (1.5 hours): Drive south on US-101 to Petaluma, then west through the dairy country of western Marin County to Point Reyes. The Point Reyes peninsula is a geological anomaly — a chunk of Pacific Plate that arrived here from far south — with elk herds, lighthouse visits, oyster farms, and dramatic coastal hiking.
Napa Valley (1 hour): Cross the Mayacamas Mountains east on Highway 128 through Calistoga into Napa Valley. The northern end of Napa — Calistoga, St. Helena — is less crowded than the southern end and retains more of the agricultural character that made the valley famous. The drive over the mountains through Knights Valley is attractive.
Santa Rosa (25 min): Sonoma County's largest city is worth an hour for the Charles M. Schulz Museum (creator of Peanuts) and the historic Railroad Square district. More useful as a practical stop — larger grocery stores, a real bookshop, the county airport.