Itinerary

Land in America’s spectacular capital, Washington DC. You’ll be driving straight from the airport over to your first stop, Loudoun County, just 30 minutes away. You’ll be arriving at a beautiful bed & breakfast set against the rolling hills of Virginia’s wine country, and be treated to stunning views during your two night stay.

Located just 25 miles from Washington DC and considered the Napa Valley of the East Coast, Loudoun County is filled with vine-covered hills, scenic vistas, charming towns and rich heritage. Get settled in and then head out for a walk around the 6-acre property or go for an easy-going hike in the idyllic surroundings to stretch your legs after your flight. Depending on when you get in, you might just want to head to one of the county’s charming little towns like Leesburg or Purcellville for some farm-to-table dining or sit on the back porch of your accommodation watching the sunset with a glass of local wine.

Loudoun County is home to more than 50 award-winning wineries, 30 craft breweries, and delightful dining so spend the day wine tasting across the region. You are within easy driving distance of at least half of those wineries making it easy to fit in multiple tastings. Widely known as DC’s Wine Country rather than as Virginia’s, the region specialises in varietals such as Cab Franc, Merlot, Petit Verdot, Viognier and the distinctive Norton grape, and offers unique winery experiences that go beyond tastings and tours. From idyllic vineyard hikes and fruit-picking at local farms, you’ll have plenty of recreational opportunities to chose from.

After breakfast make the two hour drive over to Skyland Resort in the heart of Shenandoah National Park. This seasonal lodge sits at over 3,600 feet on 16 beautiful acres inside the park and is a 5-minute walk from the famed Appalachian Trail. You’ll be entering the park from the scenic Skyline Drive – offering a glimpse of what is in store for you over the next two days.

Shenandoah has an abundance of natural beauty with beautiful chestnut and red oak forests, abundant wildlife and panoramic views. Home to over 200,000 acres of protected lands, it’s an incredible place for hiking, kayaking, listening to songbirds and watching the star-filled night sky. Get settled in and then head out to take advantage of all the wonderful outdoor activities the park has to offer.

Start your day with a sunrise hike on the Stony Man Trail or up Old Rag Mountain for some of the most breathtaking vistas in all of Virginia. Alternately, take the morning at your leisure with a short hike along parts the world-famous Appalachian Trail. Whatever you choose, you’ll find respite in your stunning surroundings.

Spend the late afternoon visiting one of the world’s most impressive underground stalactite caves at Luray Caverns just a half hour drive away. Afterwards, head into Luray where you’ll find a nice dinner to round off your day.

Drive over in the morning to Charlottesville – the trip is just under an hour and a half – and arrive at the Kimpton Forum, nestled in a Jeffersonian building on the UNESCO Heritage Site-designated grounds of the University of Virginia. Charlottesville boasts a rich, well-preserved history dating back to the late 1700s, and the city has a unique cultural, natural and architectural history showcased in its fine museums, galleries, wineries, shops, restaurants and historical sites.

Start your stay with the main reason people come visit: the historical architecture. The grounds of the University of Virginia and the stately mountain-top mansion, Monticello were both designed by one of America’s founding fathers, Thomas Jefferson, in the 18th century. Other notable places include Highland, the home of former President James Monroe, the Historic Court Square and the magnificent Michie Tavern, which has been accommodating travellers since 1794.

End the day with some alfresco dining on the city’s beloved pedestrian promenade, the Downtown Mall.

Centrally located in the eastern foothills of the Blue Ridge Mountains, it’s fair to say that nature abounds in Charlottesville, and if you haven’t already felt inclined, start the day with a wander through your hotel’s arboretum and botanical gardens. They continue towards the picturesque 25-mile long Rivanna Trail, which you can traverse if you’re looking for a tranquil hike.

Spend the rest of the day exploring the renowned Monticello Wine Trail. Home to around 40 distinguished wineries, many are within a 15 to 20 minute drive from your hotel and set against beautiful scenery. Charlottesville was recently named Wine Region of Year, and you’ll find a wide range of varieties from Bordeaux to Chenin Blanc and even the often-overlooked Petite Manseng.

Head after breakfast for Virginia Beach, where the Chesapeake Bay meets the Atlantic Ocean. The short drive over will take you to the centrally-located Founders Inn & Spa, set on 26 acres of picturesque grounds just 20 minutes from the waterfront. Get settled in and sign up to a spa treatment for later in the day. Your accommodation is well located to explore the diverse forests and marshlands away from the coast while also discovering the city’s history. Visit the site of the original colonists’ first landing in 1607 with a walk through First Landing State park or climb Cape Henry, one of the oldest lighthouses in the country.

Come evening dine at one of the many restaurants in Virginia Beach, from signature seafood and farm-to-table hotspots to laid back diners – you can even soak up some entertainment with a comedy show in Town Centre or take in a symphony performance at the Sandler Centre of the Performing Arts.

One of the East Coast’s prime coastal locations, Virginia Beach boasts three distinct beaches on which you can find some serious seaside fun. Centred around the Oceanfront with its 3-mile boardwalk stretching across 40 city blocks, warm waters await thanks to its location within the Gulf Stream. Just take your pick of beach along Virginia Beach’s sandy white coast. For calm shores and the freshest seafood head to Chesapeake Bay Beach; bike, rollerblade or people watch along Resort Beach; or for a more secluded experience, head south to tranquil Sandbridge Beach where nature and wildlife await in the nearby Back Bay National Wildlife Refuge and False Cape State Park.

Drive first thing in the morning to Williamsburg to make the most of your overnight in America’s “Colonial Capital”. Considered the birthplace of American democracy, this area is a must-visit for anyone who’s ever wondered about the foundations of the United States.

You’ll be arriving in the heart of the historic district at the elegant Williamsburg Lodge. A luxurious place to spend the next two nights, you’ll get a taste of Colonial Williamsburg as the hotel blends 18th century style with modern amenities. Drop off your bags and head out to explore – you’re just minutes away from the historic tours and exhibits. The city boasts fully-preserved historic buildings like the Capitol, constructed in 1704, the Wren Building, constructed in 1716 on the prestigious College of William & Mary campus and the Governor’s Palace, erected in 1720. It is also home to Colonial Williamsburg, a life-size recreation of the original 18th century town which offers an excellent opportunity to learn about American colonial history, the American Revolution and the inception of the United States.

Lauded for their historical significance in the development of the United States and conveniently close in proximity to one another, Williamsburg, Jamestown and Yorktown are often referred to as the Historic Triangle. Since you’ve spent a day exploring Williamsburg, drive just next door to Jamestown and Yorktown to continue immersing yourself in all four centuries of American history.

Walk the grounds of Jamestown – the first permanent English settlement in North America in 1607 – this historic site includes artifacts from the original settlers in the Archaearium archaeology museum, the remains of the 18th century Ambler Mansion which is a living-history museum, the Jamestown Settlement with recreations of a 1610s fort and a Powhatan Native American village.

Head after to Yorktown where the final battle for America’s independence from Britain took place. The town is full of 18th century homes and American Revolution history, nestled among picturesque streets, and charming local businesses overlooking the York River.

Drive over after breakfast to seat of America’s government, Washington DC, and drop off your rental car. You’ll be staying at the luxurious Fairmont Hotel in DC’s most charismatic neighbourhood, Georgetown, and will find getting around easy.

A place that in a way needs little introduction, Washington DC is world famous for being the capital of the United States and home to the iconic White House, the Capitol, the Lincoln Memorial and the towering obelisk of the Washington Monument along the National Mall. Defined by its imposing and impressive neoclassical architecture, few would fail to recognise its many memorials, monuments and buildings, which are as spectacular during the day as they are seen at night.

Get your bearings by signing up to a one-day pass on the city’s Hop On Hop Off Trolley or take a tour of George Washington’s Mount Vernon across the Potomac. Either way, you’ll get an in-depth look at some of the city’s major sights. Come evening, head to the streets of Georgetown for some delicious local dining – you can even take a food tour of the area starting in the late afternoon.

Aside from governmental institutions, Washington DC is also home to the world-renowned Smithsonian Museums and Galleries – of which there are 19 in total – including the National Air & Space Museum, the National Museum of Natural History and the National Gallery of Art. Spend the day reading the original US Constitution, perusing internationally-acclaimed art, witnessing some of the world’s best dinosaur fossils and seeing Dorothy’s ruby red slippers from the Wizard of Oz in the flesh – all attractions are free to visitors and the public so don’t miss out.

End your stay with a Monuments by Moonlight tour come evening. As majestic as Washington DC’s monuments are during the day, there’s nothing like seeing them lit up at night, and on this tour you’ll get to see them come alive as the city gets dark.