Two Shepherds’ tasting patio sits under a sprawling oak with views across the vineyard. The property has the unhurried feel of a family-run operation rather than a polished tasting room, with picnic tables scattered across the outdoor space and enough shade that you’re not squinting through your wine pour. The owners’ two Australian Shepherds are often there greeting visitors, which gives you a real sense of how the place operates. Paths wind through the vineyard itself between tastings, allowing you to walk with your dog and see the vines up close rather than just from a seated view. The winery sits on Bell Road in the Russian River Valley, surrounded by other producers but with enough space that it doesn’t feel cramped.

Dogs are welcome on the patio during tastings at no fee, and staff keeps water bowls available. They don’t accompany you indoors to the main tasting room, but most of your time happens outside anyway. The owners often explain the wines themselves, which you don’t get everywhere, and the patio setup allows you to linger with a glass. Food pairings are available if you want more than wine, making it a real lunch destination rather than just a quick pour.

Tastings run through the afternoon, so timing is flexible. Bring a sweater—even on warm days the shade under that oak can cool things down quickly. Nearby Healdsburg is about 15 minutes away, and you could string together several tasting stops without too much driving around.