St. Helena is a small town of some 6,000 inhabitants, punctuated by quaint streets and pretty boutiques, listed on the U.S. National Register of Historic Places since 1998. Less formal than Yountville, classier than Calistoga, and less designer than Napa, St. Helena is to Napa Valley what Fillmore Street is to San Francisco: quiet but lively, pretty but not staid, relaxed but bourgeois. Hungry for a bite? Farmstead at Long Meadow Ranch serves seasonal ingredients from its farm, ranch and vineyards. We also recommend Gatehouse Restaurant and, of course, The Charter Oak, which boasts three Michelin stars.

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