We like to stay close to Healdsburg square if we can (check Airbnb’s too–we’ve stayed at some gems in the past) since it’s so easy to get around. The square has so many cute shops and restaurants. I always tell people to grab lunch at Barndiva and walk over to Banshee tasting room. Such a perfect afternoon! Maybe a little Noble Folk ice cream after. We also make sure to visit UNTI and Papapietry Perry which are both tasting rooms and a 5 or so minute drive away. They are right next to each other, too! Macrostie is an absolutely gorgeous property if you want a more traditional tasting/winery experience. Chalkboard is amazing for a nice dinner, another spot I always try and book while we’re in the area!