January Is Secretly the Best Time of Year to Visit Virginia Beach

Three words: Winter whale watching

January 16, 2020 10:30 am
January Is Secretly the Best Time of Year to Visit Virginia Beach

Stipulated: the perfect travel time for a three-day weekend getaway is four hours. More, and you waste your vacation. Less, and you’re still near home. Hence our series, The 4-Hour Rule, dedicated to revealing the best destinations that are far away, yet still close to home.

Picture a beach vacation and you’ll probably conjure visions of bright blue waves and little beads of condensation dappling the side of a piña colada glass. But summering in Miami isn’t not the only way to enjoy the splendor of a weekend on the shore. At the other end of the spectrum you have the sandy path less traveled: beaches that experience real, verifiable winter weather, but in doing so offer more privacy, fewer shouting tourists and equally beautiful coastal views. 

One such place is Virginia Beach, which is a three-and-a-half hour drive from DC. It’s the perfect destination for a long winter beach weekend full of sublime kayaking, the best whale-watching opportunities of the year and restaurants that serve up freshly shucked oysters with cold local pils. Let’s dive into it.

 Visit Virginia Beach


One of the best things about beach towns in winter are the deep discounts you can get on prime hotel stays, and Virginia Beach is no exception. We recommend the Cavalier Hotel & Beach Club, which has been open for nearly 100 years and is now included on the National Register of Historic Places. Over the last century it’s hosted icons like F. Scott Fitzgerald, Judy Garland, Frank Sinatra and 10 U.S. presidents. Honestly, any property that’s a part of the Autograph Collection is alright in our book, and the luxury amenities — like an indoor “splash” pool, an on-site small-batch distilling company and a private beach club — don’t hurt either. 

Have the whole family in tow? Check out private beachfront properties on Airbnb like this dog-friendly six-bedroom home that will run you half the cost of an average hotel suite. This modern four-bedroom home also includes a large beachfront deck, grill and bar for the ultimate weekend of relaxation.

Cavalier Hotel


If you’ve chosen to stay at the Cavalier, you’re already in the same place as one of Virginia Beach’s best restaurants, Becca. This garden-to-table joint specializes in fresh seafood and ingredients from the garden out back. Similarly locavore-focused is the husband and wife-owned craft beer bar and restaurant, Esoteric, where the duo grow produce in their own attached garden, using the actual fruits of their labor to create curated-yet-approachable dishes like a pretzel-encrusted fresh catch and house-made sorbets.

Make a point of heading out to Pungo, Virginia Beach’s farm country, where you can visit one of their 16 farms offering seasonal you-pick options, from pumpkins to berries. Grab a hearty breakfast at the uber charming Bee & The Biscuit on your way to explore the farms. 

Finally, no trip to Virginia Beach would be complete without a down-home meal of unfussy seafood. Check out local favorites like Margie & Ray’s for crab legs and Southern classics like hush puppies and fried shrimp. The Shaking Crab offers an equally unpretentious option for Cajun-style seafood. 


While Virginia Beach certainly has no lack of rowdy nightlife options to choose from, there are also plenty of low-key opportunities for quality cocktails and local brews. Start out your night at the family-owned hangout Waterman’s, the perfect spot to try an iconic Orange Crush: freshly squeezed orange juice blended with vodka, triple sec and a spritz of carbonated soda. 

Keep the night rolling with a mini brewery hop, hitting up places like the oceanfront Back Bay Brewing Co. as well as Smartmouth Pilot House, a brewery located in a former post office. Reaver Beach Brewing Co. is known for their sour style, while The Bunker is owned by military veterans and features live music.

 Visit Virginia Beach


Nature buffs will rejoice at the wide breadth of options for outdoor activities in the area, from farm visits to afternoons spent at the Back Bay National Wildlife Refuge, one of the last remaining undeveloped areas along the Atlantic coast. Here, an 8,000-acre freshwater refuge features varied ecosystems like large sand dunes, maritime forests, freshwater marshes, ponds, ocean beach and large impoundments for wintering wildfowl. Access it by marsh trails on foot or by bike, or explore it via kayak.

Back Bay certainly isn’t the only place to kayak in the area either, with the bluer water of the Chesapeake presenting another great option and Great Dismal Swamp offering a slightly spookier paddling route about an hour away, its channels dotted with cypress trees. Up your chances of seeing dolphins by opting for a kayak tour with Tidewater Adventures

The main draw for many Virginia Beach tourists in the winter, though, is whale watching, which can only be done in the area from around December until March. Catch a look at magnificent humpback and fin whales that are making their annual journey north, making a stop along the way at the Chesapeake Bay. Sightseeing tours through Rudee’s offer an educational experience with the opportunity to see ample wildlife beyond the whales, including dolphins, seals and birds. 

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