Sure, we think every day is worthy of romantic gestures, but there’s something about the cooler winter months that makes us especially crave the warmth of our special someone. Not to mention, as Valentine’s Day approaches, we all go giddy for love! 

Planning your next romantic weekend escape or simply browsing some inspiration for an upcoming date? Virginia Beach has you covered with this cupid-approved itinerary (of course, the times are merely suggestions; go about your day as you please). Do it all or pick and choose your favorite; either way, your experience is sure to be sealed with a kiss.




People eating food with chopsticks.


4 p.m. Kick off your romantic Virginia Beach vacation by checking into The Historic Cavalier Hotel & Beach Club. For nearly a century, this grand hotel (which now has a spot on the National Register of Historic Places) has stood sentinel over the Virginia Beach Oceanfront. Today, it marries its timeless elegance and glamour with a warm, contemporary, and simply swoon-worthy experience. 


6 p.m. Be sure to reserve your table at Orion’s Roof, voted one of OpenTable’s Most Romantic Restaurants for 2021. Conveniently located across the street The Cavalier, the restaurant celebrates the best of land and sea, offering an elevated Asian-fusion menu with spectacular views of the Atlantic Ocean. Time it just right and catch a stunning sunset!


9 p.m. Wind down your week (and your travel day) with some elegant 1930s flair at The Raleigh Room, tucked away in the lobby of The Cavalier hotel. With plush seating, drink carts, a grand piano, and expertly crafted cocktails with a nod to decades past, this is an idyllic spot for post-dinner drinks and conversation that’ll feel like a step back in time.



A woman standing next to a man taking a picture of fish at the aquarium with her phone.


8 a.m. Cozy up within the colorful walls of May’s Parlor, a French-inspired bakery and cafe housed within a coastal cottage just steps away from the Atlantic Ocean, and enjoy a delectable selection of freshly made pastries and made-to-order coffee drinks.


10 a.m. Get in touch with your playful side and head under the sea without ever leaving the shore. Explore more than 800,000 gallons of marine life exhibits at the Virginia Aquarium & Marine Science Center. Feeling extra adventurous? Book a boat tour to see whales in the wild!


12 p.m. We think lunch can be romantic too, especially when enjoyed at one of OpenTable’s Most Romantic Restaurants for 2021! At Heirloom, enjoy a variety of creative farm-to-table dishes inspired by local Virginia Beach recipes in a warm and inviting spot.


2 p.m. Spend the afternoon getting in touch with your competitive side with a game of shuffleboard at Beachside Social; relaxing and reconnecting with a couple’s massage at one of several rejuvenating Virginia Beach spas, or exploring the Virginia Beach Town Center by foot.


7 p.m. Toast to a great day in style at Esoteric and enjoy the restaurant’s beloved offerings of handcrafted cocktails, a vast and rare selection of craft beers, and delicious shareable plates. – all in a modern and inviting local ambiance. We highly recommend saving room for dessert! 




A breakfast of french toast, eggs, bacon, hash browns, and coffee.


10 a.m. Fuel up your last day with a beloved local brunch at Doc Taylor’s. The old seaside cottage, once a doctor’s office, is well known for cranking out delicious diner-style breakfast favorites.


12 p.m. Enjoy the ultimate romantic winter beach experience on horseback with a guided horseback riding tour (no previous experience required). Together, you’ll adventure under and through the Virginia Beach Fishing Pier, then back along the beach and through the surf as you soulfully soak up natural sights on horseback.



However you choose to spend your time together in Virginia Beach, we hope you’ll take advantage of the countless romantic options our city offers and take advantage of each opportunity to relax and reconnect. Cheers, to love!