For Art & History Lovers
Arrival: Dinner & Drinks
If you’re looking to experience the elegant history of Virginia Beach, your first stop is checking in at The Historic Cavalier Hotel and Beach Club. Weekend as couples have been weekend-ing for over a century in this stately brick landmark that’s on the National Register of Historic Places.
After check-in, grab a drink at the Tarnished Truth Distilling Company on the resort’s ground floor, or take a tour of the distillery to learn how they make spirits inside a working hotel.
For dinner, head to The Hunt Room inside the hotel, a historic tavern made to feel like dining in a hunting lodge. It emanates old-world luxury and will also teach you a little about the Cavalier’s history.
Day One: Explore the ViBe Creative District and Town Center
Rise early and head to the ViBe Creative District. This neighborhood is the heartbeat of the art scene in Virginia Beach, and you can fuel up your day with coffee at Fathom Coffee. Stroll through the district and check out its collection of colorful murals and public art, popping into galleries and coworking spaces along the way.
Grab a beer or two at Vibrant Shore Brewing Company and be sure to check out the mural on its front wall. Then do lunch at DeRican Chef for some authentic Puerto Rican cuisine.
The afternoon begins with some interactive art at the Mermaid Factory, where you’ll both get a blank mermaid or dolphin sculpture that serves as your creative canvas. When you get home, you can proudly display your work as a long-lasting memory of your weekend in Virginia Beach.
Afterward, make your way to the Virginia Beach Art Center and Artists Gallery, where local artists enthusiastically explain their work adorning the walls. It’s a great way to get an inside look at the local art scene and learn why Virginia Beach has become a destination for working artists throughout the Mid-Atlantic.
Your evening highlight is a show at the Sandler Center for the Performing Arts in Town Center, where touring Broadway shows, musical performances and even some local theater take the stage. Before the show, do dinner at Tupelo Honey for some traditional southern food.
Day Two: Tour Museums & Historic Homes
Your second day is steeped in history, beginning with breakfast at Doc Taylor’s. This charming little oceanside cottage was once also the local doctor’s office and is now a de-facto place for breakfast by the water.
Keep the morning outdoors at First Landing State Park, where you can see the Cape Henry Memorial Cross marking where the first English settlers arrived in Virginia a full 13 years before the Mayflower. Then, get your muscles moving as you climb the 191 steps of the Cape Henry Lighthouse and take in the sweeping view of the ocean together.
After working up an appetite in the park, head inland for lunch at Rockefeller’s Restaurant at Rudee Inlet is in order. Here you’ll try famous Virginia Beach oysters and other local seafood.
The afternoon can be spent checking out charming, historic homes, like the Thoroughgood House, Francis Land House, Adam Keeling House and Lynnhaven House. Each gives a glimpse into how the area’s early high society lived as you learn about the industries that shaped coastal Virginia.
You can also opt to hit the Military Aviation Museum in Pungo, which houses the nation’s largest private collection of World War I and World War II aircraft. They’re all restored into flying condition, and the two of you can enjoy a shmoopy ride in an antique plane, seeing the sights from high in the air.
Finish off with a walk along the beautiful Chesapeake Bay and discuss if you believe the local legend of Blackbeard’s buried treasure. Cap off your weekend with dinner at Heirloom, where the art is in the creative presentations of fresh Atlantic seafood.
For Outdoor Enthusiasts
Arrival: Cabin Check-In & Campfire Time
The best way to immerse yourself in the outdoors in Virginia Beach is by literally living in it. So, rather than a hotel, opt for a cozy yurt or a scenic campsite inside First Landing State Park. The yurts offer a rustic yet comfortable retreat with wooden floors, a spacious deck and a skylight perfect for stargazing. If you prefer a more traditional camping experience, the park’s campsites range from primitive spots to sites with water and electric hookups, all nestled among the maritime forest or near the dunes. You won’t have TV or WiFi to distract you, so communing with nature–and each other–is easy. Grab some s’mores stuff at the onsite camp store and end your night together by the fire.
For the more adventurous, False Cape State Park offers primitive campsites only accessible by foot, bike, or boat, ensuring a secluded and immersive outdoor experience. But trust us, the bragging rights—and the untouched coastal views—are totally worth it.
Day One: Nature Hikes & Horseback Riding
Make coffee in the cabin then take advantage of the first light by hiking around the park’s lagoons and cypress trees. Walk out to the water and listen to the waves lapping against the shore before taking in the view from the top of the Cape Henry Lighthouse.
After your morning exercise, reward yourself with a healthy breakfast at the Green Cat Juice Bar & Market, where you’ll savor smoothies, salads and avocado toast al fresco. Once you’ve finished breakfast, meander along the sand to Virginia Beach Horseback and mount your steed for a relaxing trot along the beach.
After the ride, make your way to Commonwealth Brewing Company, where you can try some local beers while enjoying outdoor games on the back patio. Afterward, you can retreat back to your cabin or grab some sandwiches from Taste Unlimited and enjoy the purple skies of the sunset from the beach in the Chesapeake Bay District.
Day Two: Paddle Broad Bay & Explore Sandbridge
Your second day in Virginia Beach begins with a slow morning on the water in First Landing State Park. Rent a kayak and paddle around Broad Bay and breathe in the fresh air from the trees lining the shore, snapping photos of each other as you glide through nature.
Reward yourself for a morning of hard work with lunch from Big Sam’s at Rudee Inlet. The marina-side grill and raw bar has a massive selection of refreshing seafood, which you can sample while basking in the sunshine.
Then, it’s time to explore a new beach at Sandbridge. This relaxed community is home to rolling sand dunes and a slower pace than the Oceanfront, providing a serene environment to appreciate Virginia Beach’s coastline. If you want more time on the water, rent kayaks and explore the marshes of the Back Bay Wildlife Refuge. If you’d rather stay on land, grab some fat tire bikes at Surf & Adventure Co. and ride on the sand at Little Island Park.
A sand bike workout might leave you exhausted, so take the evening easy and let the chefs at Catch 31 create your dinner. This locals’ favorite is a great spot to enjoy coastal cuisine while staying outside, capping off your romantic weekend in Virginia Beach with one of the city’s best meals.
For Thrill Seekers
Arrival: Late Night Dinner & Drinks
Arriving in Virginia Beach at night doesn’t mean you can’t have plenty of excitement on your first evening. Check into the Moxy Virginia Beach where the lobby also doubles as a bar and social center, so you’ll likely have a whole set of new friends before you even drop off your bags.
Walk a short way from the hotel and grab some authentic Mexican food at Side Street Cantina. More than just a spot for tacos, Side Street has some of the best ceviche in the state plus a menu of tequila that always ends in adventure.
Retire back to your hotel or check out the scene at Bar Moxy and see where the evening takes you.
Day One: Go-Karts & Ziplines
Grab coffee at the Belvedere South Coffee Shop & Diner at your hotel, fueling up for a full day of adventure. First stop: The Adventure Park at The Virginia Aquarium where 33 ziplines across 17 treetop trails will get your blood pumping early and often. Race each other across the course, or just snap photos of each other speeding across the zip lines. After, calm your nerves by strolling around the aquarium before heading to lunch.
Replace all the calories you expended climbing around the Adventure Park at Chix on the Beach, a cool spot along the Virginia Beach Boardwalk with salads, seafood, sandwiches and cold beer. If you’re in town during the winter, the patio is heated so you can breathe the fresh air while still staying warm.
After lunch, head inland and keep your competitive juices going at Motor World as you speed around the Go-Kart track. Decompress while strolling the neighborhood and discussing its colorful murals.
After a quick trip back to the hotel, shower, grab a drink at the bar and head to dinner at Repeal Bourbon and Burgers. It’s one of the top burger spots in Virginia Beach, and its unparalleled collection of whiskey can be an adventure unto itself.
Cap the night off at SkyBar, the rooftop bar at the Hilton Virginia Beach Oceanfront and enjoy ocean views together with cocktails in hand.
Day Two: Watersports & Indoor Skydiving
Venture back to the ViBe Creative District and start the day at Bad Ass Coffee, a regular weekend morning spot for locals in the know.
From there, you’ve got a couple of options based on the weather. If the sun is shining, rent a couple of jet skis and challenge the waves on the Atlantic Ocean. If the weather isn’t cooperating, head indoors to iFly Virginia Beach and experience freefalling inside its high-speed wind column.
After lunch at the quirky and delicious Pink Dinghy, elevate your relationship to new heights with a parasailing expedition for you and your partner to glide softly through the air. It’s a fitting final outdoor excursion where you can sit side-by-side in the calming silence of the sky and maybe steal a kiss while you’re up there.
After returning to the hotel, enjoy your farewell dinner in Virginia Beach at Esoteric. As the name implies, the menu is a creative collection of diverse dishes ranging from charred octopus to pear and burrata salads. It’s a perfect place to share plates and get one final look at the city’s food scene before heading home.
