Imagery Estate Winery in Glen Ellen is one of those places where you actually want to spend time exploring the wine list instead of just checking boxes. They focus on experimenting with unusual varietals and pulling wines from lesser-known grape regions—the kind of bottles you won’t find at every tasting room. It’s refreshing to see a winery that puts the spotlight on wines that often disappear into larger blends, giving you a chance to discover what makes each grape variety distinct.

The tasting room has a relaxed vibe that works well if you’re bringing your dog along. You can set up under umbrellas in the vineyard area with your own picnic, which means you’re not stuck inside if it’s a nice day. The views across the Sonoma vineyards are genuinely pretty—the kind of backdrop that makes you understand why people love this region.

What makes Imagery different is their willingness to take risks with their selections. You’ll taste things here that surprise you, not just the safe, crowd-pleasing options. The staff can tell you about their approach to sourcing and why they chose certain lesser-known grapes to highlight. Bring your dog, bring snacks, and plan to stay longer than you initially thought. The whole experience feels more like hanging out with wine-focused friends than doing a structured tasting. Glen Ellen’s downtown is nearby if you want to walk around and grab something to eat before or after, and the surrounding roads are nice for stretching your legs with your dog in between pours. Check their website or call ahead to confirm current tasting availability and any picnic setup requirements for the day you’re planning to visit.