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 (voted Washington's signature dish), you’ll find it here. Explore the city while getting a true taste of the nation’s capital on one of the city’s food tours. DC Metro Food Tours offers fourteen walking food tours in the unique neighbourhoods of Washington, DC including a tour of Eastern Market, the city’s oldest continuously running food market. 

Spend three nights in Washington. 

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. The Frederick Wine Trail travels to 13 wineries and located in the foothills of the Catoctin Mountains while beer lovers should be sure to check out Brewer's Alley, Monocacy Brewing Company, and Flying Dog Brewery. When it’s time to eat, head to one of Top Chef contestant Bryan Voltaggio’s two restaurants in Frederick – the fine dining VOLT or the more casual Family Meal. 

Stay two nights in Frederick. 

Head 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. Locals love nothing more than to dive into a bushel of steamed Chesapeake Bay crabs, heavily seasoned with Old Bay. Cantler’s Riverside Inn is a popular crab shack where you can settle into a waterfront table, grab a mallet and start cracking. 

Stay one night in Annapolis.

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. Make a trip to Tilghman Island to sample Maryland’s official state dessert, the many layered Smith Island Cake, at Two If By Sea Restaurant. End the day with a seafood dinner at Stars restaurant at The Inn at Perry Cabin or The Crab Claw Restaurant in St. Michaels. 

Spend one night in St Michaels or Easton.

Continue 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”. Norfolk’s 144 mile of coastline means you’re never far from the water. Explore the charming Ghent neighbourhood where you’ll find the city’s first winery, Mermaid Winery. Take a tour and sip on a pint at O’Connor Brewing Company or SmartMouth Brewing Company. End the day with a cruise on the Spirit of Norfolk for dinner and dancing on the Elizabeth River. 

Spend one night in Norfolk. 

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. Savour the flavours of more than 900 area restaurants offering up some of the best Southern US cuisine. Sample from more than a dozen breweries including Virginia's oldest operating microbrewery, Legend Brewing Company. Stop by Hardywood Park for a wide selection of beers on tap or sample one of Strangeway Brewing Company’s unique concoctions. 

Stay two nights in Richmond. 

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. After touring the wineries, hop on the Skyline Drive through the Shenandoah National Park. This section of the Blue Ridge Parkway is considered one of the most beautiful drives in the country. There are numerous stop-off points and hiking trails along the way. Spend a couple of nights exploring the park before following the drive to its northern end in the town of Front Royal. As you head north into the Northern Virginia Wine Region, explore wineries such as Glen Manor Vineyards and Chester Gap Cellars. 

Stay two nights in or close to the Shenandoah National Park.

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. Explore Leesburg’s historic downtown area with small boutiques, restaurants and wine bars, and great outlet shopping at the Leesburg Premium Outlets for those last-minute gifts and souvenirs. 

Stay two nights in Leesburg.