Day 1 - Arrive Washington Dulles. Drive to Winchester, approx. 50 miles
Collect your car on arrival and begin your trip. Located in the beautiful Shenandoah Valley, Winchester-Frederick County is home to the City of Winchester and the towns of Stephens City and Middletown. The area is known for being the “Apple Capital”, surrounded by vast orchards celebrated during annual events such as the Shenandoah Apple Blossom Festival. Winchester is also the birthplace of country music legend, Patsy Cline. Learn more about the singer at the Patsy Cline Historic House or tour the Becoming Patsy Cline exhibition at the Museum of the Shenandoah Valley.
Stay one night in Winchester.
Day 2 - Drive to Luray, approx. 50 miles
Continue your journey through the Shenandoah Valley with a visit to Luray Caverns, the largest caverns in the eastern United States. Guided tours along lighted, paved walkways lead visitors through cathedral-sized rooms with ceilings 10-stories high, towering stone formations, and natural wonders at every turn.
Stay one night in Luray.
Day 3 - Drive to Hanover, approx. 125 miles (via Middleburg)
Take route 211 to the Thornton Gap entrance of Shenandoah National Park and then continue along Skyline Drive, a National Scenic Byway which runs along the crest of the Blue Ridge Mountains through the park. From the park, continue to Historic Middleburg. Middleburg's historic district is less than a mile long, but it's filled with many unique stores, including equestrian shops, high-end clothing boutiques, fine art galleries and much more. Take a stroll down the streets and you're sure to find something you just have to take home.
Stay one night in Hanover, Maryland.
Day 4 - Drive to Havre de Grace, approx. 90 miles (via Annapolis)
Located on the Chesapeake Bay, Annapolis is the capital of Maryland and the sailing capital of the U.S. Spend the morning touring the U.S. Naval Academy, the Annapolis Maritime Museum, or the Banneker-Douglas museum, Maryland’s official museum for African American history and culture. In the afternoon, get out on the water with a public cruise, sailing lesson, or kayaking excursion, shop the one-of-a-kind boutiques in the historic district, or enjoy a traditional Maryland crab feast at a waterfront restaurant.
End your day in Havre de Grace, situated at the head of the Chesapeake Bay. Its picturesque waterfront is best viewed along The Promenade, a ¾-mile-long boardwalk that runs along the banks of the Susquehanna River as it joins the Chesapeake Bay. Stroll the boardwalk, stopping along the way to visit the Concord Point Lighthouse, Maritime Museum, and the Decoy Museum. Finish your tour with a waterfront meal at the open-air Promenade Grill.
Stay one night in Havre de Grace.
Day 5 - Drive to Washington, DC, approx. 120 miles (via Chesapeake City)
Historic Chesapeake City, located along the Chesapeake & Delaware Canal is on the National Historic Registry, having retained an incredible proportion of its 19th-century buildings and houses which have been converted into inns and restaurants. The local museum is perfect for experiencing the town’s heritage and culture.
Drop off your car when you arrive in Washington, DC and spend your evening in one of unique neighbourhoods such as Georgetown, Adams Morgan or Navy Yard, a newly redeveloped area with a riverfront boardwalk, great restaurants and boutique shopping.
Stay two nights in Washington DC
Day 6 - Washington, DC
At once an international crossroads and America’s ultimate hometown, Washington, DC offers visitors world-class museums and monuments, Michelin-rated restaurants, gorgeous parks and gardens, and endless performing arts options. Tour the National Mall, the most-visited national park in the U.S. The Mall is home to many of the city’s major attractions including the Washington Monument, U.S. Capitol Building, and the Lincoln Memorial as well as an impressive line up of free museums such as the National Gallery of Art, National Air & Space Museum, and the National Museum of the American Indian.
Day 7 - Depart Washington, DC