How to get there: Located on the Russian River along Route 101, downtown Healdsburg is an hour and fifteen minute drive north from San Francisco. Eventually, the SMART train will carry visitors straight to the town.
What it’s got: Healdsburg has won numerous distinctions as one of the top small towns in the country. Sonoma County might not be as famous a wine destination as Napa, but the wine is just as good. Additionally, Healdsburg is at the heart of a few different wine-producing regions -- the Russian River, Dry Creek, and Alexander Valley. Plus, with so much fresh produce growing on nearby farms, the local restaurants and markets are top-quality. Try local favorite, Scopa, and be sure to visit during the annual harvest, arts, and jazz festivals.
Pro tip: The Healdsburg farmers market is considered one of the best. Held on Wednesdays and Saturdays, it’s not about frills, but it is all about local food mostly from farms within 10 miles of town.