Healdsburg is one of my favorites
To stay: Bella Luna Inn
To eat: Bravas is a must, Valette, Guiso Latin Fusion, Willi's for seafood, Catelli's up in Geyserville, and most of all, drive out to Bodega Bay and eat a crab sandwich and clam chowder at Fisherman's Cove or Spud Point, don't make a shit, eat at whichever line is shorter. It's a must. Suggest you bring a cooler (and when I say cooler, I mean a Yeti backpack) of meats, cheese, champagne (or Pliny), plastic glasses and hike the Bodega Bay Trailhead down to the beach. Pantydropper. If Armstrong State Park is open (thanks a lot, wildfires) run that same play in the redwoods.
Wine: Hall, as mentioned above, check out their sister, Walt and BACA, new room right outside of town, they're making some serious wines. CAST, Gary Farrell, Merry Edwards, Hanna, Dry Creek, Unti. The wines are stupid good up there, there isn't a wrong answer.