Itinerary

Land in America’s beautiful capital, Washington DC. You’ll be driving straight from the airport to Alexandria in Virginia, situated along the Potomac River just a stone’s throw from Washington DC. You’ll be staying in the heart of the city’s centre, a 6-minute drive from Alexandria’s famous Old Town. The USA’s third oldest historic district, you’ll find red-brick sidewalks, stunning 18th and 19th century architecture and more than 200 independent restaurants, boutiques and historic museums.

Get settled in and head out to explore. Alexandria is a walkable city, and you won’t run out of things to see and do.

Spend the morning touring George Washington’s nearby estate, Mount Vernon. You can take a bike tour up to his former home and spend a few hours learning about life when America was still a fledgeling nation.

Come the afternoon, explore more of Alexandria’s welcoming and charming downtown. A stop on the popular King Street with its delightful restaurants and specialty shops is a must and a stroll along the waterfront to the Torpedo Factory Art Centre with its intriguing collective of galleries and artists’ studios is worthwhile too. Before you leave Alexandria, don’t forget to have a drink at Gadsby’s Tavern – where some of the nation’s founding fathers used to go for a pint.

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.

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 night, 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.

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.

After breakfast make the 3 hour scenic drive along coastal Highway 13 up to Maryland’s Eastern Shore, a picturesque peninsula situated between the Chesapeake Bay and the Atlantic Ocean. Filled with historic towns, beaches and beautiful natural areas, visitors can enjoy a wide range of recreational activities, from boating, swimming and fishing to bird watching, biking and golfing. The region is also home to some of the freshest seafood you’ll ever taste, with crab being the local dish.

You’ll be staying on the Chesapeake Bay side of the peninsula at a luxury waterfront resort in the town of Cambridge. Get settled in and make the most of your exquisite location. Play a round of golf on the championship golf course nestled amongst the Eastern Shore’s innate natural beauty. Take in the breathtaking views of the Choptank River from the resort’s outdoor infinity pool or take a boat out at the stunning River Marsh Marina.

Spend the day engaging in all of the wonderful outdoor activities you didn’t get to take part in the day before. From water sports to golfing to sitting back in the resort’s award-winning spa – there’s plenty to do without even leaving the town of Cambridge.

But if you fancy a day trip, head to the Atlantic side of the Eastern Shore to the beachside town of Ocean City. Hailed as one of the cleanest beaches in America, this vibrant locale has one of the most celebrated boardwalks in the in the country, as well as some of the finest restaurants in the region, so a day out there will be well worth your while.

You can’t visit the famed Chesapeake Bay without stopping in its most famous city, Annapolis. Head over first thing – the drive is just over an hour – and spend the day exploring this scenic harbour town. You’ll be staying at the Graduate, located in the city’s bohemian Arts District and a short stroll from the U.S. Naval Academy and the Bay itself.

Known as ‘America’s Sailing Capital’, Annapolis has extensive colonial history, delightful waterfront attractions and a culinary scene that showcases the fresh local seafood. Founded less than 30 years after the Puritans landed in Massachusetts, Annapolis has significant ties to the birth of present-day America, mainly seen through the town’s beautiful 18th century architecture. Discover notable buildings like the 1779 Maryland State House and the 1773 Hammon-Harwood House or head down to the brick-paved Main Street to enjoy the bustling hub of the restaurants, pubs and shops around the harbour.

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 Capitol Hill Bike Tour or getting a one-day pass on the city’s Hop On Hop Off Trolley. Either way, you’ll get an in-depth look at many of city’s major sites at a pace of your preference. Come evening, head to the streets of Georgetown for some delicious local dining.

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.