For a fun road trip with payoff for all, wind into wine country north of Santa Barbara to this elegant estate. Sure there are delicious wines for grownups—including a complex Syrah (hints of blackberry and mocha) and Roussane, an unusual white with apricot, fig, and honey notes—but there’s also a giant chessboard with life-size pieces. If the kids don’t know how to play, just use the pieces like checkers. Get pretty views and a nice dose of nature on inviting trails to deep pools of shade beneath handsome live oaks.
Plan ahead and pack a picnic—including meats and other items for grilling (onsite grills and picnic tables are open to all). Or, on most summer and holiday weekends, enjoy creative fare from local food trucks while local singers and musicians perform on the lawn.