Rich with fascinating stories and a treasured past, Virginia Beach is the gateway to exploring the foundations of American history. Here, you can experience the past in unexpected ways—breathe it in the air, see it in charming historic homes, iconic landmarks and museums and even taste it through the area’s culinary delights. Grab your friends and family (and definitely your camera) to spend a day exploring the rich history of this coastal city.
Morning
Before you embark upon your journey through time, stop in for a hearty “coastal southern” breakfast at Bay Local. As you step inside, you’ll be greeted by the cozy, rustic charm of a laid-back coastal atmosphere, where the scent of sizzling fresh ingredients fills the air. Your plate will be stacked high with delicious, locally-sourced favorites, from fresh blueberry waffles to fried oyster “bennies”. It’s the perfect way to fuel up before diving into the rich stories that await you just minutes away.
It feels right to begin your adventure at the very spot where the first settlers arrived—First Landing State Park. Feel the soft sea breeze on your skin and inhale the refreshing scent of salty air as you gaze out over the horizon. Before you lies a sparkling, vast ocean, where the Chesapeake Bay meets the Atlantic Ocean, stretching endlessly as far as the eye can see. You take a deep breath and feel a sense of peace and belonging.
What you may not know you’re standing on the spot where our country’s first settlers originally landed, in 1607. From there, they traveled about an hour to the Historic Triangle of Yorktown, Jamestown and Williamsburg—establishing the first permanent settlement in the U.S. As you wander through the peaceful park, be sure to visit the Cape Henry Memorial Cross at Fort Story, a historic monument marking the location where English settlers made claim to the site by raising a cross on the land. Take in this powerful moment as you stand on the same ground where history was made.
Your adventure doesn’t stop there—the park is also home to the historic Cape Henry Lighthouse, the first lighthouse authorized by the U.S. government in 1792. If you’re up for a challenge, you can climb 191 steps to the top, where you’ll be rewarded with a breathtaking 360-degree view of the shimmering Chesapeake Bay and Atlantic Ocean.
Afternoon
Cruise south from First Landing Park towards the popular Oceanfront and keep your eyes peeled for the The Historic Cavalier Hotel & Beach Club, a masterpiece of modern-day elegance that has welcomed U.S Presidents and many luminaries since its opening in 1927, including legends like F. Scott Fitzgerald and Elizabeth Taylor.
If you’re craving a midday break, make your way to Chix on the Beach, located right on the Virginia Beach Boardwalk. Relax and recharge as you gaze out at gorgeous ocean views. The tempting menu features a variety of coastal-inspired tacos, handhelds, and seafood specialties which pair well with a signature crush—refreshing spirits mixed with fresh-squeezed juices and topped off with a splash of bubbly soda—making way for the perfect beachside drink.
Now that you’ve satisfied your hunger, take a leisurely stroll on the boardwalk to the Atlantic Wildfowl Heritage Museum. Nestled in the charming 1895 de Witt Cottage, the museum resides in the oldest remaining private structure on the Virginia Beach oceanfront. Admission is free (though donations are appreciated), giving you the chance to admire fascinating wildfowl art, intricate carvings, rare artifacts and stunning photos. Pro tip: Plan your visit around a live carving demonstration and be sure to stop by the gift shop for a unique, one-of-a-kind souvenir to remember your visit.
Also located on the boardwalk is the Virginia Beach Surf and Rescue Museum. Housed in a former U.S Life Saving Station built in 1903, the museum preserves the area’s maritime history through exhibits on local surfing legends, shipwrecks, storms, lifeguards and more.
Calling all aviation enthusiasts and history buffs: you won’t want to miss our next stop. Just 30 minutes south of the Oceanfront lies the expansive Military Aviation Museum in Pungo—home to the largest flying collections of World War I and World War II-era military aircraft in the world. Walk through flying hangars and see vintage planes rescued from the ravages of battle and meticulously restored to their former glory.
You’ll come face-to-face with these time machines, giving you a glimpse of moments in history that shaped our modern world. For an unforgettable experience, you can take flight in the museum’s 1941 Boeing Stearman PT-17 Kaydet and soar the skies over Virginia Beach in the open cockpit with an experienced Warbird pilot. Pro tip: book this special experience early to reserve your day and flight time.
Evening
Now that your aviation dreams have landed, it’s time to head Inland to explore historic homes like the Adam Thoroughgood House, Francis Land House and Lynnhaven House. These sites will take you on a tour through the homes of early Virginia colonists and plantation owners. When hunger strikes, indulge in a meal at Steinhilber’s, a 1939 tradition and the oldest family-owned and operated restaurant in Virginia.
As you reminisce on the adventures of the day, you’ll find solace in the water views of the Lynnhaven River and the decadent flavors of fresh seafood and melt-in-your-mouth steaks. Save some space for a homemade dessert, and enjoy a drink from their world-class bar—complete with an extensive wine list—that will have you toasting to time well spent.
If you’re up for a little more exploring, head towards the Chesapeake Bay and stop in for a brew at Commonwealth Brewing Company, an old firehouse-turned-brewery. Then head over to Chic’s Beach for a stroll along the Chesapeake Bay. Dockside Restaurant & Marina is a casual spot where you can grab a table on the waterfront deck, watch the boats pass by, and wait for a spectacular sunset show.
As your historic day in Virginia Beach comes to an end, take a moment to soak in the beauty of the evening as the orange and yellow hues melt into the horizon. It’s the perfect end to a day well spent exploring this charming and historical coastal gem.
About Our Writer
Courtney Hersl, a Maryland-based writer, is a travel enthusiast with an undeniable love for the beach, nature, and everything coastal. A singer-songwriter at heart, she finds joy in learning about new places and capturing the essence of what makes them special – in hopes of helping people plan their next unforgettable trip through authentic storytelling.
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