AFTERNOON Taste your first velvety cabernet sauvignon at Cade, a sleek, ultra-modern winery perched atop Howell Mountain. It's also the latest 204 project from fat cat PlumpJack Winery founders Gavin Newsom and Gordon Getty, so the people-watching is almost as delicious as the wine.
EVENING For dinner, head to Yountville, a tiny southern-valley town that claims to have the most Michelin stars per capita. The latest culinary superstar is Redd Wood, an upscale pizzeria from Napa star chef Richard Reddington—order the sublime asparagus, prosciutto, and taleggio pie. And save room for peaches-and-cream panna cotta with lemon-verbena granite. (Also, if you like the idea of staying in town, try the LEED Platinum–certified Bardessono Hotel, which has 62 elegant rooms dressed up with reclaimed woods and stone. Rooms from $399.)