Thomas Jefferson famously failed in his attempts to grow Sangiovese at his estate, Monticello, in the 1800s. Virginia, however, is not in that same position today.
Instead, the state's Monticello Viticultural Area encompasses roughly 1,250 square miles and includes more than 25 wineries. Just 15 minutes from Charlottesville, home to the University of Virginia, you'll find noble varieties like Viognier, Bordeaux-style blends, native grapes like Niagara, and sweet wines made from fruits like blackberries and pears.
Make home base the charming town of Charlottesville, filled with bookstores, antique shops, restaurants and loads of historic buildings. Part of the downtown area is car-free, allowing you to spend mornings strolling the brick walkway before an afternoon wine tasting in the countryside. Dinner options range from steak house to traditional Italian to multicourse affairs, with many restaurants holding a Wine Spectator award-winning wine list. And with the plethora of Virginia bottlings around, you'll have no qualms about drinking local.