The Best Road Trip Routes In Virginia

A road trip is a fun, easy and affordable way to get out and see a lot of the things around you. It can be as long or short as you want it – from weekend getaways to full-week trips. Virginia is a beautiful state with many different things to see, here are some of the top road trip ideas to help scratch that travel itch.

Virginia Beach, Chesapeake and The Eastern Shore

Ocean lovers will agree there are few things better than a beach. Start the road trip in Virginia Beach, one of the longest stretches of beach anywhere, with over 35 miles of coastline to enjoy. Once you’ve had your fill of the boardwalks and waterfront, drive east via the Chesapeake Bay Bridge-Tunnel to the Eastern Shore of Virginia. Here you can enjoy the pristine beach with undisturbed wildlife. Continue on north with a stop at the quaint town of Charles City, and then further to Onancock from where you can take a ferry for a day tour of Tangier Island. Tangier Island is a small oyster and fishing island that will take you back in time, along with the sounds of gulls and other bird life. Finally, go further north and stop near the Virginia-Maryland line, at Chincoteague and Assateague islands where you can see wild ponies!

Skyline Drive

Wineries

There are over 200 wineries across the state so for a winery road trip, it’s best to pick a region, have a designated driver, and start tasting your way through. The Loudoun Wine Trail is an easy getaway from Washington, DC and is home to a number of scenic wineries, little towns with fantastic dining, and plenty of bed and breakfasts for comfortable overnight stays. The Monticello Wine Trail in Central Virginia has over 30 wineries across North, South, East, West trails and is home to some fantastic stops, and conveniently located near Charlottesville.

Shenandoah Valley

Start the trip in Staunton and make your first stop the Natural Bridge, a must see site in Virginia. From here continue on to the towns of Lexington, Hot Springs and finish in Roanoke. Along the way there are history and culture stops with the Frontier Culture Museum, Woodrow Wilson Presidential Library and Museum, the American Shakespeare Center, Virginia Military Institute and Museum and Humpback Bridge, as well as battlefields and historical markers at every stop. You’ll also find interesting roadside eats along the way, plus good dining options in the towns. For a luxurious overnight, stay at the Homestead Resort. The Shenandoah Valley is really a beautiful part of Virginia and well worth the trip.

Road Trip to Presidential Homes

Virginia has been the home of eight US Presidents, and most of their homes can be visited. Start just south of DC at Mount Vernon, the historic home of George Washington with ground tours, museums, and a working farm. From here go south to Richmond and stop at Berkeley Plantation, the birthplace of William Henry Harrison, and also Sherwood Forest, estate of John Tyler, to see where the ninth and 10th Presidents respectively grew up. A few minutes outside Richmond, you can visit Thomas Jefferson’s childhood home, Tuckahoe Plantation. Continue west to visit Jefferson’s crown jewel, Monticello, and further on to James Madison’s Montpelier. The landscape in this part of the state is gorgeous with mountain vistas around, wineries, and more. End the trip at Staunton, the birth place of Woodrow Wilson with a tour of the Presidential Library and insight into his early life.

Since you are here, we would like to share our vision for the future of travel - and the direction Culture Trip is moving in.

Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.

Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.

Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Private Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.

We know that many of you worry about the environmental impact of travel and are looking for ways of expanding horizons in ways that do minimal harm - and may even bring benefits. We are committed to go as far as possible in curating our trips with care for the planet. That is why all of our trips are flightless in destination, fully carbon offset - and we have ambitious plans to be net zero in the very near future.