We like to stay close to Healdsburg square if we can since it's so easy to get around. The square has so many cute shops and restaurants. We love an Oakville Grocery visit (for sandwiches to go or to pick up snacks for the weekend). They also have a new little wine tasting room next door! Obsessed with Little Saint (where Shed used to be!) for coffee, shopping, and they also have a lounge for plant-based bites and wine. For a sit down lunch, Barndiva is a favorite. We also make sure to visit UNTI and Papapietro Perry which are both tasting rooms and a 5 or so minute drive away. Flowers, Reeve, and Macrostie are lovely properties if you want a more traditional tasting/winery experience. Molti Amici is amazing for a fun date night—it's a vibe!