Charlottesville, Virginia

Courtesy of Pippin Hill

Looking to infuse your winery-focused bachelorette weekend with an air of Southern refinement? Look no further than this college town, home to the University of Virginia, and the surrounding Albemarle countryside. When it comes to accommodations, your options range from the posh Keswick Hall, which reopened last summer with clay tennis courts, an infinity pool, and a swanky new restaurant by internationally lauded chef Jean-Georges Vongerichten, to the artsy Quirk, a colorful and contemporary hotel with a scene-y rooftop bar and cooler-than-it-should-be gift shop. 

If you’re going the Airbnb route, book in the Belmont neighborhood. It’s situated away from the college kids, but still walkable to coffee shops and restaurants. 

Must-visit wineries include King Family Vineyards, where you can enjoy polo matches, refreshing rosé, and a lively lawn scene; Pippin Hill, which is run by the same folks behind Charleston’s stylish Zero George hotel; and, a bit further out, Early Mountain Vineyard, where the cheese and charcuterie platters are best paired with the four-pour “Virginia” flight and savored on the outdoor patio. (Open to expanding your palate? Both Potter’s and Castle Hill offer stellar cider and beautiful natural scenery.)  

Come dinner, indulge with a multi-course tasting menu at Broadcloth, or go casual with seafood at Public Fish & Oyster. And if you need a break from boozing, Charlottesville’s downtown pedestrian mall has plenty of adorable boutiques, and the hike to Humpback Rock is sure to help you sweat out any lingering hangovers.


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