Meet up with your trip leader at Union Station in Washington, DC for a 6:30am start. Leave the city behind as you drive two hours south to Richmond, Virginia, where you’ll gear up and get on your bike. Enjoy views of rolling countryside stitched with split rail fences, and spot some of Virginia’s most historic plantations: pass grand Shirley Plantation, Berkeley Plantation and Westover Plantation.
Ride past Sherwood Forest Plantation, where President John Tyler retired along the banks of the James River, and follow a bike path into Charles City, the site of fierce clashes between Black Union troops and Confederate soldiers. Break for lunch at Cul's Courthouse Grille for fresh Southern food in a converted country store and home.
Make the final push to Jamestown, the first permanent English settlement in the present-day United States, then end your tour at the Williamsburg Winery. Enjoy a well-deserved private tasting of the winery’s distinctive reds and whites, then tour the cellar and sit down to dinner at the onsite Gabriel Archer Tavern, which serves light, flavorful pub fare in a onetime farm shed. Return to Washington, DC in a private vehicle for drop-off by 8pm.