A visit to Barboursville Vineyards is no ordinary wine tasting experience. Located in Orange County, about a 30-minute drive from Charlottesville, the award-winning winery draws more visitors annually than Montpelier, the nearby historic home of President James Madison. Two family villas on the estate include one designed by Thomas Jefferson for Governor James Barbour (now in ruins) and another that has been turned into the elegant 1804 Inn. The estate also features the lovely Palladio Restaurant, serving Northern Italian classics for lunch and dinner. Guided tours of the winery are offered on weekends, while tastings in the Tuscan Room are offered daily ($7), except for a handful of national holidays. Visitors are encouraged to stroll the historic grounds while sipping as well: must-try vintages include the bold red, Octagon, and Barboursville’s highly praised Viognier. For a truly special day or weekend getaway, splurge on the Library 1821 tasting (only on Fridays, Saturdays and Sundays) that pairs exclusive reserve vintages with culinary treats ($25), wander the grounds, stay for dinner and sleep peacefully in a romantic four-poster at the Inn.