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Itineraries

Warm Up to Romance with This Virginia Beach Winter Itinerary

Author Valeria L. Palmertree with long blonde hair smiles, wearing a floral print blouse against a black background.

Valeria L. Palmertree

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.

Friday

A table spread with a plate of grilled toast, a dish of sliced vegetables with shredded cheese, and a small bowl of mixed salad. Two hands holding chopsticks are reaching for the salad.
A table spread with a plate of grilled toast, a dish of sliced vegetables with shredded cheese, and a small bowl of mixed salad. Two hands holding chopsticks are reaching for the salad.

@orionsroofvb

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.

Saturday

Two people stand in an aquarium tunnel, taking a photo of fish swimming overhead.
Two people stand in an aquarium tunnel, taking a photo of fish swimming overhead.

@vaaquarium

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! 

Sunday

Breakfast plate with French toast, scrambled eggs, bacon, and butter. Side of hash browns and pancakes visible. Cup of coffee nearby.
Breakfast plate with French toast, scrambled eggs, bacon, and butter. Side of hash browns and pancakes visible. Cup of coffee nearby.

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!

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  • Luxury
  • Winter
Author Valeria L. Palmertree with long blonde hair smiles, wearing a floral print blouse against a black background.

Written by Valeria L. Palmertree

Valeria has cultivated her passion for storytelling throughout a 15-year communications career that has granted her the opportunity to find, write and tell stories on behalf of a variety of brands, including destinations across the country. A native of Buenos Aires and raised in Miami Beach, Valeria has called Virginia Beach home since 2014. At first unsure of what she’d find here, she quickly grew fond of our coastal city’s laidback style and learned that everything she thought she knew about seafood and farm-fresh ingredients wasn’t enough. Over the past seven years, she has had a front-row seat to seeing some of her favorite restaurants emerge, alongside a collective of local artisans who have provided VB with its distinctly vibrant vibe. A lover of food culture, some of Valeria’s go-to spots include Commune, Esoteric, The Atlantic on Pacific, May’s Parlor and Jorgio’s (leave it to the native Argentine to find herself a taste of home). When she’s not savoring the local dining scene, Valeria can be found chasing sunsets over the Chesapeake Bay, writing, reading, cooking, traveling, listening to live music and taking in the outdoors with her husband and golden retriever – First Landing State Park is one of their most beloved spots! As a communications consultant, Valeria helps clients unearth, craft and share their stories. Learn more about Valeria’s work – and read her musings on food, travel and more – at ThePalmTreeType.com.