Nestled in America's Historic Triangle in an area that was first colonized in 1633, The Williamsburg Winery stretches across 320 acres of picturesque farmland known as the Wessex Hundred. The vineyard's first grape-crushing dances took place in 1987, and they've since developed to produce 25 sip-ready varietals along with a lengthy list of vintage library wines ideal for tucking in a cellar or serving to a homesick time traveler from 1993.

In a setting styled to evoke the mood of an 18th-century European winery, tours meander along a pebbled walkway alongside simple stucco structures before ducking inside a quaint wine museum. Inside the tasting room, private wine cellar, or the Gabriel Archer Tavern that overlooks the grounds, oenophiles can swirl, sip, and throw their heads back to gurgle aged libations from a large roster of wines.