Road Trip Itinerary From New York City To Virginia Beach

Interstate 95 (I-95), one of America’s oldest, is the main thoroughfare that runs up and down the East Coast of the United States. Some of the major hubs along the way are Baltimore in Maryland, Washington, D.C., Wilmington in Delaware, Richmond in Virginia, and more. Before packing your bags and hitting the road, here are some of the must-see attractions to jot down on your itinerary, from New York City to Virginia Beach.

Philadelphia, Pennsylvania

Get to Independence Hall, birthplace of both the Declaration of Independence and the Constitution, early for a free ticket. To guarantee entry and avoid waiting in line, purchase a ticket online or by phone for $1.50 in advance. Grab lunch at Sonny’s Famous Steaks, located just steps away from the Liberty Bell, and enjoy an authentic Philly cheesesteak. Afterwards, stop by the infamous Eastern State Penitentiary, which once housed many of America’s most notorious criminals. Today the eerie, fortress-like structure is a crumbling historic landmark that allegedly receives visits from long-gone former inmates. Take a tour of the grounds and explore the empty guard towers, hallways and cell blocks but beware; you never know when you might feel an icy tap on the shoulder.

Independence Hall in Philadelphia, PA, the birthplace of the Constitution and the Declaration of Independence

Baltimore, Maryland

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Washington D.C.

Visiting the nation’s capital is an absolute must on your road trip to Virginia Beach. During your visit to D.C., explore Capitol Hill, walk by the White House and spend time in the world’s largest museum, the Smithsonian. Have a picnic lunch on the two-mile long National Mall or buy a hot dog from a street vendor. If it’s a rainy day, there are countless restaurants to choose from in the area. Relics at the International Spy Museum have been revealed to the general public for the very first time, so take a couple hours to explore the building and see devices of espionage, including cipher machines, counterfeit currency and weapons. For dinner, enjoy a nice dinner in Georgetown, one of the oldest neighborhoods in the district.

Colonial Williamsburg, Virginia

Colonial Williamsburg is the the world’s largest living history museum, and was the center of political events leading to the American Revolution. Visitors can explore the perfectly-preserved 18th-century city today and get a glimpse of what life was like for America’s first settlers. Start at Market Square and begin your walk down Duke of Gloucester Street, the main road through town. Along your stroll you’ll see Colonial-style shops open to the public including a grocer, apothecary, bakery, and several full-service tavern restaurants. Actors donning 18th century attire walk the streets and play their parts as townspeople, soldiers, officials, shopkeepers and homemakers. For a meal, stop in one of the colonial taverns, or walk to Merchant’s Square where you can nosh on sandwiches, wine and cheese at The Cheese Shop; or try a traditional Welsh Rarebit from Dog Street Pub.

Experience what life was like for the earliest settlers in the U.S. in Colonial Williamsburg

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.