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Celebrate America’s 250th in Virginia Beach: A 3-Day Itinerary

This July, cities across the country will celebrate America’s 250th birthday — and as a colorful coastal city that’s also a significant U.S. history hub, Virginia Beach is the perfect place to join in the festivities. Check out this  3-day itinerary, offering the best of our beachy bounty while highlighting how this region’s rich heritage has contributed to the American story. 

But where will you stay? First, check yourself into the Historic Cavalier Hotel and Beach Club, then go forth and write your own tale.

A beautiful landscape featuring a large historic building surrounded by vibrant flower beds with white and purple pansies under a sunny sky.
Everyone should experience the incomparable Historic Cavalier Hotel.

Friday, July 3: Fabulous Firsts

Virginia Beach moves at an easy Southern pace, so you’ll start your day with a leisurely breakfast at Becca, right in your hotel — serving fresh, farm-to-table fare in an elegant, light-filled setting. Everything on the menu is memorable, but the Cavalier Benedict (with fresh jumbo lump crab) is a coastal cuisine must, and you should probably get an order of the Old Cavalier Bourbon French Toast (battered with custard steeped in made-on-site Tarnished Truth Bourbon) “for the table.”

We’ll also ease into adventure by staying close to your Cavalier “home” today. Just five minutes’ drive from this luxurious pinnacle of civilization, you’ll find First Landing State Park: a registered National Landmark, breathtaking natural wonder and home to the spot where the first English settlers made landfall in the New World. Spend the morning exploring the park’s nearly 20 miles of hiking trails, meandering through salt marsh, dune, freshwater pond, tidal marsh and bald cypress swamp habitats — and be sure to keep your eyes peeled for countless wildlife species. 

View from inside Old Cape Henry lighthouse with large windows, overlooking Virginia Beach with the New Cape Henry lighthouse, greenery, and the ocean under a cloudy sky.
American history stands tall at Cape Henry with its two legendary lighthouses.

Next, with some natural history under your belt, follow the Cape Henry Trail to the nexus of national history: the First Landing Site. Today, a simple granite cross marks the place where the Jamestown settlers originally walked ashore on April 26, 1607. From there, it’s just a short walk to another important first: the Cape Henry Lighthouse, which was the first such structure authorized by the new U.S. government in 1792. Climb its 191 steps for panoramic views of the breathtaking Chesapeake Bay.

Dinner tonight is just a quick jaunt down the Oceanfront to The Bunker Brewpub, one of our many veteran-owned businesses, serving elevated pub fare and handcrafted beer to a soundtrack of live music. Afterwards, follow your ears to our free Oceanfront Concert Series, which has welcomed national acts like George Thorogood and String Cheese Incident in past years.

Saturday, July 4: Splashes, Stars and Stripes

A hand holding a fresh oyster above a plate of oysters on ice, accompanied by sauces and a colorful garnish.
There’s no better way to celebrate a special summer than with fresh seafood, right on the water.

Like our country, Virginia Beach contains multitudes — and today’s the day you *really* make a splash. We’ll kick off the adventure with something you can only do in our charming coastal city: unleash your inner hero with Patriotic Excursions. This is no ordinary boat tour; instead, you’ll become part of an exciting military-style simulation aboard authentic U.S. Navy RHIBs (rigid-hulled inflatable boats.) Gear up for a 2.5-hour adrenaline rush as you tackle water-based challenges inspired by real-life special ops missions, including recon, rescue and tactical maneuvers.

Once you’ve defeated your imaginary adversaries — and hopefully, spotted a few dolphins in the process — you’ll definitely be ready for lunch. Luckily, you’ll already be tucked away in a secluded inlet of the Chesapeake Bay: a key player in American naval history and a pretty amazing place to have a waterfront meal. The Back Deck is just a two-minute drive away, but it’s about to transport you all the way to Seafood Heaven; five kinds of fish tacos are on offer here, along with local wild-caught Lynnhaven oysters and middle-neck clams, made to be relished with bayside views.

Next, we’d recommend a robust siesta to freshen up for even more fun tonight. Every year, our beloved Stars & Stripes Celebration welcomes visitors and locals alike for a rousing celebration of America’s birthday. Starting at 7:00 p.m., there’s free live music on three Oceanfront stages: 17th Street Park, 24th Street Park and 31st Street Park — and at 9:30 p.m., a brilliant fireworks display lights up the entire Virginia Beach Boardwalk and the sparkling Atlantic Ocean beyond.

Sunday, July 5: Colonial History and Creative Cocktails

A stylish couple enjoys drinks by a cozy fireplace in a warmly lit lounge, featuring rustic decor and a vibrant atmosphere.
History is always in the air in Virginia Beach — especially in the Hunt Room.

With another big day ahead, you’ll want to fuel up for the fun — and there’s no better place to do it than Pocahontas Pancake House. This cozy, beloved breakfast spot does have a full breakfast menu in addition to fluffy flapjack stacks and crispy Belgian waffles. But with all the walking you’re about to do, there’s never been a better time to indulge in something decadent like Peanut Butter & Chocolate Chip Pancakes or Efesto’s Pecan Banana & Strawberry Waffles. Remember: calories are literally just energy. 

Your morning fare is especially fitting, as today you’ll travel to the Historic Triangle — about an hour’s drive north — to learn about Pocatontas herself, and her role in Colonial American history. Within a relatively small area, you can explore Jamestown Settlement and Historic Jamestowne; walk in the footsteps of Revolutionary War soldiers at Yorktown Battlefield and the American Revolution Museum at Yorktown; and trace the founding of a new nation in Colonial Williamsburg

Whether you visited everything in the Triangle or a select few sites, you’ll be happy to see the beautiful brick facade of the Cavalier welcoming you back home for the evening. And tonight, on the final evening of your Virginia Beach semiquincentennial adventure, you’ll dine in style in The Hunt Room, on hotel property. This intimate, Southern-inspired tavern serves traditional steak and seafood classics alongside award-winning Tarnished Truth spirits, which are handcrafted onsite. 

Other Ways to Celebrate America with Us

Four people stand in an aircraft hangar, observing a vintage propeller plane with a yellow and black checkerboard pattern on its nose. Other airplanes are visible in the background.
Spend a day learning about America’s flying history at the Military Aviation Museum.

Road-tripping down from Sail4th250 in New York, or coming in June for Sail250Virginia? There’s more fascinating history and maritime heritage in Virginia Beach than you can see in just three days. Consider extending your visit to take in some of our other on-theme offerings, including the Military Aviation Museum and Virginia Beach Surf & Rescue Museum, as well as the Thoroughgood House and Lynnhaven House — both of which provide a unique opportunity to experience Virginia Beach much as our very first residents saw it, in the nation’s earliest days.

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Author Staff member, Staci Amend is smiling with shoulder-length, wavy, blond hair wearing a patterned blouse.

Written by Staci Amend

As a Californian living in Colorado, writer Staci Amend takes a “why not both” approach to the whole mountains vs. oceans debate. She covers travel, nature, beauty and fashion for a variety of publications and brands — and is happiest when surrounded by hand-painted tile, struggling to pronounce her next meal. A Huntington Beach native and longboarder, she tries to time her Virginia Beach visits with the East Coast Surfing Championships.