The Ultimate American Road Trip: 9-Day Virginia Itinerary

Just across the Potomac River from America’s capital of Washington, DC, you’ll find the Commonwealth of Virginia. So close, you just have to cross a bridge. But what you’ll find with that crossing is an entirely different world. A world of cobblestoned streets and scenic mountain drives. Small towns and beach-side cities. A land that embodies what authentic America is all about. Come travel with us to Virginia.

Day 1

Start your trip in Alexandria, a city rich in history and culture. Old Town Alexandria, a nationally designated historic district founded in 1749, today hums with more than 200 independent restaurants and unique boutiques alongside intimate museums and a vibrant waterfront. At the heart of it all is bustling King Street, a walkable mile recognised as one of the “Great Streets” of America.

Old Town’s cobblestone streets and beautifully preserved 18th and 19th century architecture make Alexandria a city ideal for exploring on foot. Stroll back through time with one of the cities many guided historic walking tours to discover the role Alexandria played in a budding new America. Companies like Discover Alexandria will even tailor a tour based on your specific interests.

Dip deeper into Alexandria’s fascinating history through some of its many intimate museums. Just off Market Square, where every Saturday they hold one of the nation's oldest continually operating farmer's markets in America, you’ll find several captivating museums that help you discover George Washington’s world. Alexandria was, after all, the home of America’s legendary, first president. Tour the Carlyle House, one of the grandest mansions in early Alexandria; the Stabler-Leadbeater Apothecary Museum, the colonist’s pharmacy; and Gadsby’s Tavern Museum, the local tavern frequented by America’s first six presidents. Visit the George Washington Masonic Memorial to view historic artefacts and take the elevator to the top for spectacular views of the Capital Region. A Key to the City museum pass, available at the Alexandria Visitors Center, gains you access to many of the city’s major attractions.

Once you’ve worked up an appetite, stop for some of the area’s succulent seafood at Hanks Oyster Bar or The Fish Market. Cocktails at modern speakeasy Captain Gregory’s are a great way to toast your new discoveries.

Lay your head at one of the many hotels that honour Alexandria’s storied past with historic décor. Indulge in The Autograph Collection’s Morrison House or The Alexandrian, both conveniently located on, or just off, King Street in the heart of Old Town. Or book a room at the Hotel Indigo Alexandria, on the waterfront, featuring playful nods to the city’s shipping past.

Day 2

Stroll the shop-filled streets or hop the complimentary King Street Trolley and head to Alexandria’s waterfront for a visit to the internationally renowned Torpedo Factory Art Center. Constructed in 1918 for the manufacturing of torpedoes, the centre now features 82 working artists' studios and galleries as well as the Alexandria Archaeology Museum.

Embark on a Potomac Riverboat Company cruise to George Washington’s Mount Vernon, the most visited historic estate in the nation. Tour the centuries-old grounds, gorgeous gardens and interactive museum before enjoying lunch at the Mount Vernon Inn, with colonial charm, costumed servers and delicious regional and colonial cuisine. Afterwards, visit George Washington’s Gristmill and Distillery, once the largest distillery in America and a major source of Washington’s income. Artfully restored and producing whiskey today, you can purchase a sample at the gift store.

If you’re feeling energetic, take the Bike and Boat Tour and cycle back to Alexandria along the scenic George Washington Memorial Parkway keeping an eye out for the often-spotted American bald eagle.

A river view from your restaurant is the perfect way to wrap up a waterfront day. Grab dinner at Vola’s Dockside Grill, Blackwall Hitch, The Chart House or Hummingbird, located at the Hotel Indigo.

Day 3

Shopping is an art form in Alexandria and well worth the dedication of an entire day. Recognised as one of the area’s top shopping destinations, Old Town boasts a blend of independent galleries, stylish shops, vintage venues and national retailers. Discover hard-to-find international labels alongside well-known big-name brands and everything from antiques to doggie boutiques.

Take a moment to revel in the gorgeous outdoors. The Washington by Water Monuments Cruise is one of the best ways to take in the waterside beauty of Alexandria and the famed monuments of DC. Or hop a water taxi and ride across the Potomac river to the National Mall to explore the numerous Smithsonian museums, where you'll find everything from dinosaurs and historical artefacts to fine art and film memorabilia. The water taxi also can take you to National Harbor for a little gambling at the new MGM National Harbor or for outlet shopping at Tanger Outlets.  

You started your time in Alexandria walking in the footsteps of Washington. Now fast-forward through history and dine in one of the many Old Town restaurants favoured by today’s presidents and first families. Try a few courses at Vermilion, a favourite “date-night” spot for Barack and Michelle Obama, or opt for dinner at Union Street Public House, where Joe Biden dined.

After spoiling yourself with some of the best food in the country, seek out a little live entertainment at a local pub or catch a show at The Birchmere, America’s legendary music hall where top-named entertainers perform nightly.

Days 4 & 5

Set out for Shenandoah National Park and the charming small town of Luray, Virginia, just a couple hours west of Washington, DC. 

A wilderness playground in the middle of the Blue Ridge Mountains, Shenandoah National Park is one of the most popular and scenic areas in America’s National Park system. Drive the serpentine Skyline Drive as it crosses and re-crosses the crest of the Blue Ridge Mountains, stretching like a ribbon among the scenic mountain peaks before becoming the legendary Blue Ridge Parkway and continuing through the Virginia mountains. Trek more than 500 miles (805 km) of hiking trails, including parts of the famous Appalachian Trail, and encounter pristine waterfalls ascending to ancient granite summits. Once you arrive, it'll be easy to see why you should spend more than a single day exploring the area.

Stop for lunch at Skyland Lodge, offering stunning views of the famed Shenandoah Valley below. Or, refuel after a hike with flatbreads and charcuterie from The Valley Cork. 

In the evening, head for the park’s gateway city of Luray, a Virginia Main Street Community and registered National Historic District where festivals, performing arts, paved walking trails, an art museum, murals and monuments are accessible year-round. Century-old buildings house antique, boutique, and outdoor stores. A selection of locally owned and operated fine or casual eateries are all within walking distance of B&Bs, inns and hotels. Stay at the historic Mimslyn Inn, for a taste of true Southern hospitality, or the boutique Hotel Laurence.

Day 6

Start your day on the storied Shenandoah River, famous in legend and song, a destination for fishing, canoeing, kayaking and camping enthusiasts. Travel the cool rhythms of a time long gone passing forested banks and green and golden farm fields. Companies like Shenandoah River Outfitters provide rentals, transportation and all the necessary equipment.

Next stop: Luray Caverns, eastern America's largest and most popular caverns system. This US Natural Landmark is noted by the Smithsonian Institution for the variety of formations and unsurpassed natural colour. Discover cathedral-sized rooms filled with towering stone columns, shimmering draperies and crystal-clear pools and hear the haunting sounds of the world’s largest musical instrument, The Great Stalacpipe Organ.

Day 7

Time to head for the coast to live the beach life! Three and a half hours south of DC, Virginia Beach’s mild temperatures make for year-round outdoor enjoyment. Rent a beach cruiser and bike along the shore at low tide, where you'll find beautiful views of the Atlantic Ocean and a wealth of fun, beach-front activities. Stop along the way for lunch at Waterman’s Surfside Grille and try their signature drink, the Orange Crush. And don’t forget to buy some saltwater taffy from one of the many souvenir shops to fuel your pedalling.

Cycle beyond the boardwalk for a stop at the historical Cape Henry Lighthouse, commissioned to be built by George Washington, where a climb to the top rewards with gorgeous ocean views. Then on to First Landing State Park, and the exact site, marked by a cross, where the English colonists first landed in 1607.

As the sun sets, find yourself back on the boardwalk for a photo with King Neptune, a 34-foot high, 12-tonne iconic bronze statue, and a little live music at Neptune Festival Park followed by fresh seafood from one of the many boardwalk restaurants.

Now you’re more than ready to rest for the night in your ocean-front room as the sound of waves rocks you to sleep.

Day 8

After starting your day with a stack of pancakes at Pocahontas Pancake House, take a farm tour — an oyster farm, that is — with Pleasure House Oysters. Take a boat out to the oyster grounds and indulge in newly shucked oysters served up on a table sitting in the water. You can’t get any fresher than that! You’ll also get a hands-on education in oyster farming and learn some facts about the local wildlife.

Then it’s off to kayak with dolphins. The playful creatures are often easily found just off the shore in the Chesapeake Bay. Chesapean Kayak Tours has developed a reputation for knowing just where to spot them. The gentle waves of the bay help ensure your kayak experience is as friendly as the dolphins.

End your day with a favourite American pastime — a little leisurely shopping at Lynnhaven Mall or Town Center, featuring outdoor cafes, restaurants, upscale retail and nightlife.

Day 9

Where else can you dine in an old doctor’s office? A former 1920s beach cottage now houses a favourite local breakfast spot named after its history, Doc Taylor’s. 

After fuelling up on just what the doctor ordered, head to Sandbridge, south of the boardwalk. Here you’ll find quiet beaches with sandy dunes and waving grasses. Numerous holiday rental homes line the streets and beckon you to come back soon and spend a few weeks this time! You’ll also find the Back Bay National Wildlife Refuge where you can hike and enjoy glimpses of wildlife along the waterway banks.

You might not expect an aviation museum in a beach city but the Sandbridge area is home to The Military Aviation Museum, one of the world’s largest collections of warbirds in flying condition. It includes aircraft from Germany, France, Italy, Russia, the United Kingdom and the United States, from both World War I and World War II. You can even fly in one with an appointment.

Celebrate your last night in Virginia with a real American seafood experience. Dine at Margie and Ray’s, originally a country store and tackle shop, where today, visitors and locals alike flock to the restaurant when Chesapeake Bay blue crabs come into season. Or try Blue Pete’s with a view provided by Mother Nature. The body of water on which Blue Pete’s is situated, Tabernacle Creek, was appropriately named after a place of worship. Combined with fresh seafood, it’s the ideal salute to the heaven that is Virginia!

Want more? Explore a 3-day itinerary of parks and trails in the Capital Region or take a 7-day road trip through the best of Virginia, Maryland and Washington, DC.