You’ll know you’re here when traffic halts. St Helena (ha-lee-na) is the Rodeo Dr of Napa. Fancy boutiques line the historic downtown's Main St (Hwy 29) and provide excellent window-shopping. Parking, however, is next-to-impossible summer weekends (tip: look behind the visitors center).
The least gentrified town in Napa Valley feels refreshingly simple, with an old-fashioned main street lined with shops, not boutiques, and diverse characters wandering the sidewalks. Bad hair? No problem. Fancy-pants St Helena couldn’t feel farther away. Many don’t go this far north. You should.
This onetime stagecoach stop, 9 miles north of Napa, is now a fine-food destination playing to the haute bourgeoisie, with more Michelin stars per capita than any other American town. There are some good inns here, but it’s deathly boring by night. You stay in Yountville to drink at dinner without having to drive afterward – town is walkable.