Man, look at those guys on a full beam reach,” Parker mused. “What a perfect day to sail!” He was right. The sailboats on this leg from Anegada to Jost Van Dyke in the British Virgin Islands were fully heeled and solidly outgunning our pace aboard a similarly sized power catamaran. The sun was shining, and puffy cumulus clouds punctuated a deep blue sky hanging over green hills and rolling surf as far as the eye could see.
Our twin screws pushed us through the playground of billionaires and millionaires, Parrotheads and newlyweds, people escaping the law, and people like us escaping the grind. The British Virgin Islands as a name even sounds enticing. It’s a place where sunsets are a sweet, powerful kiss goodnight, and sunrises are a warm, orange embrace from Mother Earth. It’s a place we can run barefoot in the sand, drink piña coladas whenever we please, and safely swing our bow in whichever direction looks most agreeable.
On that day, it was toward Jost Van Dyke, the nautical day-drinker’s magnetic north. The icons on our weather app seemed stuck on repeat, forecasting sun and salty breezes that both warmed and cooled us simultaneously, and made our crew thirst for yet another cold Carib beer.
Parker orchestrated our counterclockwise circumnavigation of paradise. He not only plotted our trip and assembled the novice crew, but he also looked right at home at the helm. Accompanying him on the flybridge were his wife, Karen, and bubbly friend Milka, who kept Parker’s ego in check by lobbing continuous, well-humored insults his way.
Before leaving the MarineMax Vacations charter base in Tortola four days earlier, Parker’s official captain’s meeting discussing our departure went something to the effect of: “No one talk. Only Matt talks. Watch your corner, and make sure we don’t hit anything. Let’s go.” Matt is Milka’s husband, pressed into service as our chief blender operator and my counterpart in buoy wrangling. The most harrowing part of our entire trip would be leaving the tightly packed base in an unfamiliar monster of a boat, though Parker made it look easy. He, of course, declined assistance from the lovely local staff, as any proper mouth-breathing, knuckle-dragging man would.
On a whim, we diverted from our heading to Jost, the longest run of our week, for a brief stop at Sandy Spit. The deserted, heart-shaped sandbar is so idyllic, you’d swear it was Photoshopped into the landscape. From there we motored into Jost Van Dyke’s White Bay, where swimsuit-clad tourists dotted the shoreline, fronted by a string of some of the most famous beach bars in the Caribbean. Among them, Seddy’s One Love, Ivan’s Stress-Free Bar and, of course, the Soggy Dollar, where wet dollars from swim-up patrons have been the most widely accepted form of currency for decades.
Sitting under a row of newly planted palm trees, we’d reached a point in our trip where time was better measured by Painkiller intake than a watch. Around three-Killer o’clock, Parker happened to notice that many of the other bareboats had cut and run for the protected night anchorage of Great Harbour. We followed suit and spent the evening on the bow, watching shooting stars. The next morning, Matt and Milka kayaked into the sleepy village for a selection of breakfast pastries from Christine’s Bakery before we untied and dropped the mooring ball.
We chose to charter this MarineMax Aquila 443 power cat so we wouldn’t be at the mercy of the wind, even though the island nation is widely regarded for its steady breezes. Though some of us had flirted with sailing, we were all more comfortable with throttles and wheels at our fingertips in lieu of sheets and winches. With twin Volvo Pentas to push us through any headwinds—or lack thereof—and a spacious three-cabin interior, we knew we’d be predictably fast and comfortable. The thought of air conditioning didn’t hurt either.
On our first night in the BVI, we were pleasantly surprised to find the week’s provisions already delivered. A free service with an easily met minimum order, it required some advance online planning but saved a lot of hassle on our departure morning. At go time, a personalized onboard orientation of the cat included essential information we’d need for the week ahead. My biggest takeaways—which way to point the bow in the event of fire, and how to work the head—remain prized additions to my boating knowledge.
Once Parker, Matt and I took turns stumbling through the Raymarine Hybrid Touch chart plotter, our trip’s first waypoint was locked on Virgin Gorda. The plan was to overnight in Spanish Town, celebrate with dinner at a chic beachfront restaurant, CocoMaya, and turn in early. That would tee us up to grab a coveted mooring ball at the Baths—the stunning rock formations that are the country’s most recognizable natural wonder—at daybreak.
In the morning, I was awake in time to see the boutique cruise ship Club Med 2 drop anchor as we passed, threatening to inundate the Baths’ intimate beachfront grottoes with a crush of tourists. Parker hustled us to pack dry bags and swim ashore so we could enjoy the morning calm. As we exited the trail through the boulders at Devil’s Bay, completely in awe, we intersected with our first tour group. Our signal to turn back, we ate lunch overlooking the giant granite stones before motoring to Leverick Bay, where we’d be within reach of Anegada the next day.
“Drive on the left. Keep it under 30. We have wild cows, wild sheep, wild donkeys and wild people. They all roam freely,” said Lawrence Wheatley, owner of Anegada Beach Club, as he handed us the keys to the five-seater Suzuki we’d use to explore the backroads of Anegada. “I’m born and raised in Anegada, and I’ve snorkeled every inch of this beach,” he continued, directing us to his favorite spot in Loblolly Bay.
Many of the experienced skippers we’d encountered gushed about Anegada despite its flat, featureless figure and surrounding fortress of ship-smashing reef. As we passed deserted white beaches, with water in various hues of electric blue, we started to understand.
Our search for a lobster lunch from the surrounding reef led us to Big Bamboo, a restaurant and bar fronting the 10-mile ribbon of sand where Lawrence had pointed. We swung in chairs suspended from massive sea-grape trees while waiting for the succulent lobster to grill. Anegada, indeed, lived up to its low-key reputation.
I’m taking a break from responsibility today,” Parker announced on the flybridge. “You and Matt get us out of Jost and over to Norman.” Ready to get some time at the helm, Matt and I took turns navigating and steering between Tortola’s West End and Great Thatch Island, pulling up outside Norman Island.
It’s here we found the best snorkeling of the week, exploring submerged caves and thick schools of blue tangs. We took a break to move to our overnight mooring within the Bight, a large and protected anchorage encircled by uninhabited island. “It’s pretty easy, isn’t it?” Parker asked, referring to the precise control dual engines gave our big rig as we pulled in.
We opened the galley to the aft deck, unfolded the backsplash, and ponied up to the bar (ah, an ingenious touch). Matt and Milka blended some icy piña coladas, and with a slight buzz, Parker and Karen took the paddleboard as a mothership for a long snorkel along the rim of the harbor. As the sun sank low, we all hiked up the spine of the island, watching its last rays shoot across St. John.
Morning light was soft on the Indians, four pinnacles of rock just outside the Bight that break the surface like icebergs, with more below than above. Karen led our most epic snorkel yet along a vibrant reef teeming with sergeant majors, parrotfish, blue tangs and varied corals. We spent hours exploring the formations.
Before returning to the base at Nanny Cay, we sought out one final must-do: a visit to the William Thornton Floating Bar & Restaurant, known universally as the Willy T. It’s a renowned dive bar of indiscretion—and infamous in BVI lore. In deadpan, I overheard the bartender ask a patron if he’d like crushed Viagra sprinkled atop his drink. There was a moment of awkward silence.
“When I was younger, all I saw was fun here. Now at age 55, all I see is liability. And I think about my daughter,” joked Rick Schott of Charlotte, North Carolina, who sipped a drink next to me at the stern bar. Two patrons plunged to the water from the upper deck. It was too early for them to be naked.
At two-Killer o’clock, the need to return the Aquila power cat was greater than the desire to do things we’d later regret. We headed for the base. With a gusty wind chopping up the marina entrance, Parker made his best call of the trip, and had a crewmember dinghy out to steer us home.
We ended our adventure at the mercy of the very wind we sought to control, but were happy that the friendly help at the base kept the week worry-free. We ribbed Parker all the way in for leaving hatches open in the rain and always forgetting to leave a light on, but we were glad he was always the consummate skipper and responsible for remembering such things.
Zach Stovall is a photographer and freelance writer based in Florida.