Day 1 - Arrive in Washington, DC
Begin your holiday in the Nation’s capital, packed with famous sights, free attractions and museums, world class shopping, and great restaurants and nightlife. And as the capital city, it’s no surprise that DC’s dining scene is as colourful and eclectic as America itself. Whether it’s a stunning view from a rooftop bar or a fine dining experience in a Michelin starred restaurant, a cosy evening in a historic pub or Ben's Famous Chili Half Smoke, you’ll find it here.
Spend three nights in Washington.
Day 4 - Washington, DC to Frederick Approx. 50 miles
From DC, begin your exploration of the Capital Region by heading northwest to Frederick, Maryland. Named one of the top 25 “Small Art Cities” in the US, Frederick is a historic and cultural hub home to more than 25 museums and historic sites. Embark on a 3-hour guided walking tour and culinary adventure through the historic downtown with Taste Frederick Food Tours.Day 6 - Frederick to Annapolis Approx. 70 milesHead southeast from Frederick to Annapolis, Maryland’s capital city. Long known as a sailing destination, Annapolis is host to splendid colonial buildings clustered around the 18th-century Maryland State House. The city’s scenic waterfront, which includes the US Naval Academy and Main Street, is packed with art galleries, boutiques, restaurants and historic memorials. Head to Ego Alley to watch the yachts or book a sailing tour.
Stay one night in Annapolis.
Day 7 - Annapolis to the Eastern Shore Approx. 40 miles
Finish your journey of Maryland along the state’s tranquil Eastern Shore region. The town of Easton is considered to be the heart of the Shore’s art and culture scene and is an ideal base for exploring the region’s small towns and natural beauty both on land and water.Day 8 - Eastern Shore to Norfolk Approx. 185 milesContinue travelling south along the Eastern Shore to the city of Norfolk, Virginia. Along the way you’ll cross the Chesapeake Bay Bridge-Tunnel, a 23-mile-long bridge and tunnel system designated “One of Seven Engineering Wonders of the Modern World”.
Spend one night in Norfolk.
Day 9 - Norfolk to Richmond Approx. 90 miles
From Norfolk, travel to Richmond, the capital of Virginia and home to many of the region’s historic attractions, world-class food, a growing slate of breweries and outdoor adventures along the roaring James River and Virginia Capital Trail.
Stay two nights in Richmond.
Day 11 - Richmond to Shenandoah National Park Approx. 150 miles
Head west from Richmond towards the Blue Ridge Mountains to tour the Monticello American Viticultural Area (AVA). The eastern slopes of the Blue Ridge and the rolling countryside to the east offer excellent topography, fertile granite-based clay soil and a growing season of over 200 days. You can visit several wineries and vineyards in the area, including Barboursville Vineyards, producer of Octagon, the most renowned red wine of Virginia.
Day 13 - Shenandoah National Park to Leesburg Approx. 70 miles
From Shenandoah National Park, travel north to Leesburg where you’ll discover why Loudoun County is considered DC’s Wine Country. The rolling countryside offers a lovely backdrop to the areas wineries. Some of the best views and wines can be sampled at wineries such as Breaux Vineyards, Sunset Hills Vineyard and Stone Tower Winery.
Stay two nights in Leesburg.
Day 15 – Leesburg to Washington Dulles Approx. 15 miles
Posted by: America As You Like It
Posted on: 11/04/2025