Virginia Beach, VA | City Guides for the Urban Nomad

Most people have no idea that New York has amazing beaches. Why? Because the conversation is too crowded by everything else. Our coastline is interrupted by an iconic skyline. Our sand has been fused into layers of concrete supporting floors of skyscrapers. Our rays of sunlight have been outshined by the bright lights, big city.

So what is there to be said for a city known and named for its beaches? Likely a lot more.

I was unapologetically led to Virginia Beach seeking to extend my summer. The empty lifeguard stands at the Rockaways made me feel prematurely abandoned. It still felt warm. According to the calendar, it still was summer. If the season had fled, I would chase it.

Admittedly I was driven to this southern city for such a purpose. Yet even as I descended upon it, I was reminded of the futility of this designation.

To define a place simply by a fortunate geographical feature is nearsighted and foolish. Manhattan is surrounded by water but not one of its inhabitants is living an “island life”. And Virginia Beach has a coastline, and what else?

Upon entering the Oceanaire Resort at the waterfront, I was stopped by a concierge sitting in a small booth near the entrance. “Hello ma’am, welcome to Virginia Beach!” he said.

“Well thank you,” I told him.

“Need any recommendations on things to do in the area?” He shoved a pack of tacky family-focused beach guides and business listings into my hands.

“Oh honey,” I wanted to say, “You have no idea why I’m here, do you?”

Temporarily armed with the antiquated local travel materials and leaving my defenseless competitor in my wake, I set off to rewrite to story of the area over the next three days.

What I found was a city with a beating heart. A creative community that was accepting and admittedly more successful through and from the successes of their peers; people who blurred the lines of surfer and hustler but were enraptured by the limitless potential of the area; a food scene based upon the bounty from surrounding waters, creatively enhanced with boundless international influences; and a general feeling of eternal, enlightened summer.

Come spend three days in this vibrant, coastal city and find what you didn’t expect.

This day will be dedicated to appreciating the Coastline beyond the beach. Inevitably a coastal town develops a character that is largely driven by the tides, but what about this culture and history is missed when we’re simply sitting upon the sand, looking out at a horizon line that, when blurred, could be realigned nearly anywhere? Absorb today the history that put this city on the map and see the coastline in a distinctly Virginia Beach way.

Nearly 100 years ago, The Cavalier Hotel first opened its doors and brought an undeniable sense of opulence, luxury, and prestige to the city. With a direct rail line leading to the hotel, guests from the Midwest and Northeast flocked here for luxurious getaways and to be a part of the social scene. Through long, wine-laden dinners, friendly croquet matches, nights dancing under the moonlight and seductive smoking lounges, it elevated the city way, way above sea level. Each room featured a claw-footed bathtub that would draw salt water directly from the ocean, if you preferred. The hotel grabbed the attention of seven US presidents as well as Frank Sinatra, Elizabeth Taylor, and other celebrities who laid their heads to rest within its brick walls. F. S. Fitzgerald was inspired by the space and feeling at the Cavalier that he was said to have written part of The Great Gatsby while lounging at the indoor pool, pen and gin in hand, presumedly.

After WWII broke out, the hotel was commandeered by the military and used for radar training (and likely some salt-water bathtub training too…) and in the years after that, began to fall into disrepair. The city’s boardwalk and oceanfront strip was booming and the comparatively brutalist structure did not match the balcony-speckled highrises of the times. A family feud for ownership ended in a court-ordered sale of the hotel in 2012 to The Cavalier Associates, who after 6 years and $84 million in renovations, re-opened its doors in April of 2018.

The Cavalier has flawlessly recaptured the historic opulence of what the property once was and what it is now. Every reimagined corner, every piece of artwork, every inch of vintage decor embodies a slightly ironic sense of retro glamour. It has revitalized the undeniability of an accommodation becoming a destination. Having a drink at The Fox Hunt brings you back to the historic social club among taxidermied animals and hushed conversation. Sitting upon black-and-white striped chaise lounges by the glamorous indoor pool fills you with a certain Fitzgeraldian inspiration. Having breakfast in the sun-drenched veranda at Becca gives you the confidence that you will be leaving nothing but glamour and historic potential in your wake for the rest of the day. Get the Becca Benedict for a little stack of heaven that is centered upon one of the area’s finest delicacies – local blue crab. Reservations recommended, book yours here. The Cavalier is located at 4200 Atlantic Ave.

There’s no way to experience the transition of the different time periods, neighborhoods, and landmarks of Virginia Beach than by biking its historic boardwalk. Rent a cruiser from Cherie’s and coast along the coast from 4th to 40th Streets and take in the juxtaposition of sand-and-ocean that has never and will never change (just hush up for now about the ice caps, k?), and everything beyond the boardwalk that is constantly evolving.

Cheesy econo lodges are just a few pedals aways from luxury resorts; iconic ice cream stands compete with farm-and-ocean-to-table experiential restaurants. Pause as hipsters in high-legged one-pieces and cutoff Levi’s cross over the bike path and take a full stop for parents juggling babies and tugging wagons full of sand toys with their portable Tommy Bahama beach-chair-and-cooler-fusions on their backs. Somehow there’s room for it all here. Cherie’s is located all along the boardwalk, but we picked ours up and dropped them off at 4th street location. Info here.

Your trip is going to be a welcome mouthful of mostly oysters and crabcakes but to taste someone transitioning the local bounty into something a little more inventive, head to Aloha Snacks for a refreshing Hawaiian-style “snack” in a former service station. This place is a local surfer’s destination, and we overheard multiple conversations about the surging waves hitting before Hurricane Florence would (not directly!) make landfall. One table was reviewing photos as a local surfer was repeating excitedly, “Dude, I told you I got barrel on that one! I knew I did!” The owner, Jesse, embodies the healthy-but-not-smug vibe of the place, telling me about the menu before leaving me with this overarching explanation – “We just keep it real man.”

Among multiple poke bowls and some Spam iterations that I hadn’t seen outside of Hawaii (I’ve missed you, musubis!!), they plan to add ramen and bone broths in the Fall. The most important thing not to miss here? The Portuguese “malasada” donuts. These custard-filled little pillows of delight are some of the best pastries I’ve ever had. Aloha Snacks is located at 501 Laskin Rd.

Take in the coastline in its most natural state by heading south to Sandbridge. This mostly-residential area is a neighborhood bordered by nearly untouched beaches. There’s no boardwalk, no benches, no burger joints, no lifeguard stands, no rentable comforts. It’s Virginia Beach stripped down and located just south of the strip. It also has access to False Cape State Park, a stunning, secluded park on a peninsula with campsites and kayaking all along the Backbay waterway, stretched over 4.5 acres of untouched land. It’s one of the area’s best-kept secrets, just 15 miles from the touristy shorefront yet it feels worlds away.  After the quick 20-minute drive, we parked and crossed the dunes onto the nearly-secluded beach. Bring everything you’ll think you’ll need, but also realize that that’s little more than a towel, bottle of water, sunglasses and sunscreen. Ok, and a screwtop bottle of rose.

Instead of diving right into the water, sometimes the best way to gain a new perspective on a coastline to get out and above it. Way above it. In an open-cockpit WW1 Biplane. It wasn’t hard to feel the pride and presence of the military as soon as I landed at the Norfolk airport. Signs, murals, men in uniform, and the sporadic, deafening sound of military jets flying overhead were constant reminders of the presence and history of the military in the area. But if you’re not a history buff or military brat, the best way to fully appreciate the importance of this part of the city’s soul is to take a tour of the Virginia Aviation Museum and take a ride in a real WWII Biplane. Helmet and goggles provided, insisting on being called “Goose” for the flight’s entirety is encouraged, and the views are guaranteed not to be forgotten. Tours run Saturdays only, April 2nd-Oct. 31st. Book your flight here.

Cure those post-WWII-flight nerves and head to an iconic spot where the windblown-look is always in style. Waterman’s has been serving up Virginia Beach’s now iconic cocktail, the Orange Crush, since the early 80s, right on the waterfront. The space feels historic, shying away from the bright and flashy tourist trap restaurants along the strip. To sit and sip at the steadfast wooden bar here feels like a trip back in time. Get an orange crush and some oysters or steamed crab legs and admire the black-and-white photography on the walls highlighting the history of the area. Get tipsy enough to finish all of your souvenir shopping at The Beach Nut, the charming little shop inside the restaurant, owned and curated by the owner’s wife. Waterman’s is located at 415 Atlantic Ave.

A local favorite. Rudee’s has somehow weathered the storm of the changing tides of the area for over 35 years, concentrating on what it does best: fresh seafood in a no-frills atmosphere served with good drinks by good people. The vibe of the place is like an old fisherman’s social club, situated right beside a marina on its namesake inlet. Sit outside, eat seafood, do it at sunset. Rudee’s is located at 227 Mediterranean Ave.

Located in the basement of the Cavalier Hotel, end your night where you started it, just a bit further down, in a space that’s bit more seductive, feeling a bit more sunkissed. After absorbing the history and magic that has washed up on the shore in Virginia Beach, think it over in a historic speakeasy and wash it down with the same spirits and haunts were made in the area. The Hunt Club feels like a step back in time with its gnarly brick walls, oversized antique fireplace, unironic taxidermied decor and old-world-wise mixologists.

I was craving the bitter-booziness of a Negroni but wanted to try something from the on-site distillery, so I went for the Boulevardier: 2 parts Tarnished Truth whiskey, 1 part Campari, 1 part sweet vermouth, 5 parts oversized globular icecube. This drink was the perfect mix of nostalgia and innovation, which is the best way to get into the spirit after a full day of exploring.

Today will be spent appreciating how Virginia Beach has evolved along with its natural surroundings. There’s a reason that you won’t find a city overrun with strip malls and luxury townhomes, chain restaurants and big box retail. The city has sought to preserve and protect its integrity and infrastructure and inevitably, it’s natural surroundings, since its original tourism boom in the 60s. Immerse yourself in its natural beauty today.

Virginia Beach has not only been a historically relevant destination for vacationers for over a hundred years, it was also the first place the settlers landed and temporarily settled in, establishing the country’s first elective government in April 1607 before pushing up the James River to Jamestown. Now First Landing is a state park and home to 19 miles of interpretable hiking trails and a maritime community including a Cypress swamp and tidal marsh that is among the most endangered habitats in the world. Walking along the footsteps of our founding fathers filled me with the same creative energy that is now revitalizing the area, and the expansiveness of the natural surroundings and foliage ceiling made me forget all about my concrete city roots. Plan your trip here then get lost.

I live in a city surrounded by water that I’m not able to get in or really experience, and would certainly not consider eating from. Even the surrounding oceans have warning signs for pregnant women, elderly people, those with previous health conditions of any kind, humans with digestive systems, pets who aren’t rabid and thus need to die, and basically any being that wants to keep living, to not eat what you find beneath its surface. Virginia Beach has worked to preserve and protect its precious waterways in spite of its 450k residents and 19 million annual visitors. Need proof? How about a boat tour through the Lynnhaven River with captain and oyster farmer Chris Ludford who will scoop, shuck, and slurp down his beloved bivalves right there with you while wading in the water. Farm to table is cute; water to mouth is way, way better. Experience the first-hand the sweetness, the brineyness, the saltiness, the richness, the beauty and complexity of this watery delicacy. Experience it first-hand by the expert-hands that maintain and sustain them. Book your tour here before you visit and expect to wade.

Pungo is the area’s farming community, and exploring the area felt like a super spread out Brooklyn neighborhood. The people of Pungo are artists and passionate foodies, making sure that the area serves its community wholly, sustainably, and with a quirky bit of style. My favorite two spots are Sawdust Road Coffee, a charming little cafe in a converted farmhouse. This place embodies what I like to call the “diet south” vibe that Virginia does so well- a little bit country but not overdone; tastefully kitschy, artfully tacky, and completely personal. Get an iced lavender latte and wander around the space, admiring local art and photography. 1791 Princess Anne Rd.

Pop into The Bee and The Biscuit for a light, locally-sourced lunch in a cottage restaurant from the early 1900s. This place fills up fast, especially on the weekends, so go early, grab a sandwich and a local beer and appreciate the history of the space and the area. 1785 Princess Anne Rd.

Stop by the Pungo Board Shop to understand the core of surfing culture in the area. Husband and wife owner’s Dylan and Kari will set you up with surfing lessons, help fix your board or shape a totally new one, and will do anything to make you feel at home at their shop or in the ocean. 1789 Princess Anne Rd.

Here’s the deal. I’ve grown up around oysters. I appreciate them, I understand them, I am enamored by them. I dine out because of them and return for them. I have also lived abroad and currently live among a culinary landscape naturally curated by cutthroat competition whereby only the strong, the passionate, the perseverent and the talented survive.

Even considering all of my experienced bites, Terrapin in Virginia Beach is one of the best meals I’ve ever had.

A local establishment toeing the balance between the city’s ambitious creative vision and it’s local reality, we dined there on a Wednesday night which happens to be Fried Chicken night. Sound kitschy? Reimagine it through the lens of a James Beard award winning chef; a fluffy-crunchy 1/4 chicken perfectly paired with a pleasantly truffled mac-and-cheese and a glass of pinot noir for $22. This brought in a distinctly local vibe to what could be seen as an unapproachable restaurant, but instead it’s one that you can tell is disinterested with sullying its target market; Terrapin wants to feed and delight its community.

I understood and appreciated the Wednesday Night Special but for all I’d heard of about Terrapin, I needed to be a free-range customer. I shared the charcuterie plate, which included a nearly-melted duck prosciutto and bold beef brasaola; the housemade burrata which came with a welcome pomp and circumstance from the plumpest, ripest, and most regionally seasonably vegetables and crusty, warm bits of sourdough; a crop of shishito peppers of whom’s ripeness I’d yet to understand again outside of Spain; local oysters with a housemade tomatillio minionette that created a perfect flavor waltz as the oyster danced its way upon your senses; and that was just the begininng. We moved onto the second course between sips and then glasses of Pinot Noir. We chose to share the sea scallops with wild, local mushrooms, oven-dried tomatoes and a lightly truffled pan sauce, along with the cannot-be-missed lamb entree in which the meat played took centerstage but even without, the curried eggplant and sweet potato could have held their own. Next came a parade of desserts which almost made us forget about the rest of the meal. Almost. The service was flawless and respectfully more felt than seen. Dinner at Terrapin is for anyone who appreciates an utterly complete dining experience where you will leave with nearly nothing but awe and satisfaction. This is destination dining. Terrapin is located at 3102 Holly Road.

For after-dinner drinks and (maybe) a tapa or two, head to Pacifica. I was recommended this spot to get a feel for the local spirit of the city and for unpretentious yet expertly-crafted cocktails. What I received was an outpouring of pride and anecdotes from people who you could tell truly cared about their community. The bar was slightly buzzed and buzzing with the threat of an oncoming Hurricane, a category 5 that was tracking to hit land within a day. However, no one was concerned with evacuation routes or high-wind warnings, instead explaining to me exactly why there was no reason to be concerned. “Virginia Beach will never suffer a direct hit,” I was told confidently, again and again. I learned that the area was spiritually protected, as recognized by the prophet Edgar Cayce, a man known as the father of holistic medicine, who didn’t accidentally choose to settle and build his temple in the city. That the area was a hurricane-proof sanctuary was not a matter of religion or faith, but a matter of fact. “It’s not going to hit us,” I was reminded when I asked for advice about changing my flight. “It just won’t.”

No one was concerned even as flood warnings and evacuation mandates flashed across the television screen. Everyone chose instead to listen to this prohpet’s perpetual forecast. This collective spiritual unconsiousness here that found its way into nearly every conversation. Even as the wind was picking up on my walk home, I felt calm somehow believing in the powerful prophecies of Edvard Casey. And also in the powerful, calming effects of a well-made negroni. Pacifica is located at 214 40th St.

Virginia Beach took the bold move of taking an entire industrial neighborhood that had been abandoned and forgotten and seeing it through a different lens. In true “leap and the net will appear” fashion, it seemed crazy that the city along with developer and philanthropist Andrew Fine, believed into the microneighborhood that is now known (even Jeopardy known!) as the Vibe Creative District. And that belief and energy manifested in the curiosity of creators, inventors, entrepreneurs, movers and shakers that were welcomed in with open arms and outdoor murals and good coffee and a contagious mentality that this could be something, that it will be, that it is something.

A regionally-progressive bakery for a town whose breakfast landscape was formerly defined by 24-hour pancake spots, May’s Parlor is a pastry lover’s dream. Owner Racheal Browning, a 26-year old Chesapeake-Native with an unmatched talent with French pastry, greeted us when we entered and I noticed her eyes light up as soon as she saw the slight panic of delicious indecision upon my face. “Croissant dough is kind of our specialty,” she told us without bragging. This I soon learned was the most humble way possible of saying, “This is the best goddamn croissant you’ll eat outside of France.”

As we made our croissant-centric selections (without also ignoring the cream cheese cinnamon bun, the orange-frosted brioche and a not-so-classic BEC), an older man came in. He pointed to something behind the glass. “Would you like that heated sir?” Rachael asked him.

“Oh, these are just display, huh? The real ones are frozen?” he asked with a perceptible Southern accent.

“No sir, we make everything here fresh daily,” she replied patiently.

“Oh. So why do you heat it in the microwave?” he asked pointedly.

“We have a convection oven.”

“Oh.”

A regionally-progressive bakery in a town where an older crowd of tourists and residents alike will take time to appreciate and realize the beauty of what a bakery can be and is. May’s Parlor is located at 2708 Pacific Ave.

Three Ships is a perfect example of a place that is catering to both the emerging, creative urbanist population of the city and the curious tourist. What I’d heard about Three Ships is that they serve lattes with cereal sprinkled on top. “Sounds cute,” I thought, genuinely. When I entered the vintage-nautical space, the barista welcomed me and asked if I had any questions as I stood in front of a wall of onsite-roasted bags of beans. “I have a French Press?” I answered. He laughed and then came over to me, handling each bag gingerly while explaining to me the roasting technique, the flavor profile, the nose and finish each cup would have as a vintner indulging guests in the complexities of each vintage’s terroir.

This was not the kitschy fruity-pebbled experience I expected. I paid for my “God Speed” Ethiopian-Costa Rican blended bag and learned that my purchase came with a free drink. “Iced coffee, black,” I told him. As I left happily sipping, I heard the girl behind me ask, “Y’all are the ones who do that Cinnamon Toast Crunch drink right?” Yes. Yes they do. Three Ships Coffee is located at 607 19th St.

Hidden just behind Three Ships coffee is The Alley, the beating heart of the ViBe district and home to two of its most iconic businesses – North End Bag Co. and Igor’s Signs and Stripes.

It’s a creative cooperative in an old service station that is now fueling the momentum of a new district and perspective of an entire city. The two businesses had a vague connection with the town before they set up roots in the alley. Each can understand first-hand the frustrations and appreciations for the dynamic of their environment. Both wholeheartedly recognize that if it wasn’t for the welcoming, appreciation,

It feels like these days, there’s an equation to perfection. Bright lights, white marble surfaces, small plates, farm names, and iterations of avocado toast will make the people and their iPhone cameras flock to your establishment and therein lies your branding. Right? Well, not if you give a damn. Or are bold enough to go against the grain and to fight the tide in order to build something that has never existed before. Husband and wife business owners and entrepreneurs Dwayne and Rachel Appleton have been shaping the brand behind Java Surf Cafe for six years, and every corner, color, creation and crumb in their charming cafe is evidence of that.

More than a coffee spot, their community-focused space also is a gallery for local artists, a yoga studio in the evenings, and a meeting place for local organizations and happenings. Sit outside among the rainbow of tables and chairs, in front of one of 60+ murals in the district and understand the creative community and spirit that defines the ViBe district and those who often start and end their days with this emphatic couple. Java Surf Cafe is located at 1807 Mediterranean Ave.

Chris Richeson, the master distiller and inventive mind behind Chesapeake Bay Distillery is by a highly intellectual loose cannon of sorts and the type of wild spirit cannot be contained. Yet, for some reason and somehow, he has made his business in containing the unpredictability of spirit distillation. He has a distinctly mischevious look in his eyes, always; like he’s about to get caught doing something he’s not supposed to be doing. And after all, when you look at it closely, should anyone be distilling liqour that is constantly winning this many awards, available for an insanely reasonable price, out of an unsuspecting repurposed industrial space in Virginia Beach? I’m onto you, Chris. And way into your spirits. Read the full story in my Profile of a Hustler series here  (coming soon!) and in the meantime, recreate the spirit and mischevious flavors that imbibe and invigorate the renaissance of the area here with a drink recipe from the master himself:

3/4 oz pureed English cucumber

2 oz. Blue Ridge Vodka

3/4 oz. lime

1/2 oz. Triple Sec

1 Basil Leaf

Shake, strain, serve up with a fresh basil leaf

Chesapeake Bay Distillery is located at 437 Virginia Beach Blvd.

They say that the first trackable food review was written in a journal kept by John Smith after sampling some Virginia oysters. Those oysters, from the Lynnhaven River, were something to behold and remember and certainly to write home about. Thus it’s not surprising that so many culinary havens have now popped up to feature and celebrate the respected bivalves. Atlantic on Pacific is a new destination that is now helping to define Virginia Beach’s culinary scene, a place built from the waters but expanding the minds and tastes of all who cross through the brightly lit, brass-and-marble accented space aptly located on Pacific Ave. Their menu is locally sourced and rooted in Southern inspiration with nearly no geographical boundaries. We had the Blue Crab and Corn hush puppies with honey-jalapeno (which were far from your Southern BBQ joint’s dense, weathered pups), the colorful and delectable crab toast, and the indulgent steak tartare to add a little land-lubbing to the mix.

I chose to imbibe with an oyster dirty martini that tasted like the sea and came with a raw, freshly shucked and bamboo-speared oyster. Atlantic on Pacific has an exciting, internationally-inspired and regionally-based menu and a refreshing cocktail list that builds you up from the garnish down. Local flavors, honest food, and an experience (and happy hour!) that will keep you coming back. Atlantic on Pacific is located at 3004 Pacific Ave.

Among the best part of the changing creative landscape of the area is the introduction of authentic international cuisines and cultures in the area. Far from the categorized brochure of restaurants I was handed upon arrival that included Chinese take-out spots and a few further inland Taco Bell locations, these restaurants are creating experiences that will immerse you in cultures far from the Eastern Virginia coast. Auntie Tiki’s, a lively new Filipino spot and tiki bar, is the pinnacle of creating the unexpected immersive travel experience just steps from the eastern shores of Virginia. Known for its non-kitschy tropical cocktail menu, Auntie’s also features a dinner menu and exotic yet familiar social scene that is miles away from the cheesy beachfront bar. Get carried away at a place that feels far away, with people who seem just like family.

Auntie’s Tiki is located at 4312 Holland Rd.