Circle St John

Cody howard Unfiltered

Circling St John
Three strangers circumnavigate a Caribbean gem


Words by Mark Anders
Photographs by Robert Zaleski


Ted Rutherford’s first instinct is to duck. He counts 12 shots, a quick barrage from a semi-automatic weapon. Probably a .22, he reasons, and less than 200 yards away. Having spent 15 years in the military, Ted knows instinctively that this is not target practice. In the long silence that follows, he goes back to eating his omelet. Then the sirens start to wail.

Circling St John

I sleep through the gunfire, and when the sirens finally wake me I step into another gorgeous January morning on St. John. The sea and sky are that perfect Caribbean blue you see in the brochures, and puffy white clouds skid across the sky on the sweet-smelling trades. Still, gunfire with breakfast isn’t how we imagined our 40-mile circumnavigation of the island would begin, and by the time the details reach our ears—it was indeed a murder, and the assailant is still on the loose—Cruz Bay is wearing on us. The picturesque little harbor town is a strange mix of Tommy Bahama-clad tourists, drunk college coeds, cooler-than-thou American expats, and locals who clearly wish all of the above would just leave. Personally, I don’t blame them. I can’t wait to get onto the water.


Before we can go, though, Ted has to liberate his standup paddleboard (aka SUP) from Customs. I can’t explain why we’re required to clear Customs in the U.S. Virgin Islands, which after all is an American territory. Likewise, it’s not easy to explain why standing on an oversized surfboard and propelling it with a 6-foot-long canoe paddle is a rational way to make a multi-day circumnavigation. Kayaks are the logical choice, but like thousands of others who tried SUP after seeing super-surfers like Laird Hamilton doing it in magazines, I have become hooked. As a lifelong kayaker and surfer, I took to this hybrid of the two sports easily. Cruising the bays near my home in coastal North Carolina, I found the standing position affords a unique view, both above and below the ocean. In some ways, it feels as if you’re walking on water.

Circling St John


I’ve also always had a thing for visiting commonplace destinations in uncommon ways. In Venice and Amsterdam, I used a kayak to escape the tourist throngs and explore the canals on my own. On a trip to the Boundary Waters, I attempted to live off the land while paddling with a Chippewa elder (see “Gone Native,” in the December 2008 C&K). So in this case, rather than just visiting a relatively well-trodden Caribbean island, I decided it would be more fun to paddle around it. On a standup paddleboard.

St. John seemed like the ideal location for such a journey. The water is warm, the weather predictably beautiful, and at just 21 square miles, it can be easily circumnavigated in five days. And although there are enough hotels and restaurants spaced out along our clockwise route to make logistics simple (our most important piece of camping gear was a credit card), the real beauty of this expedition is that the Virgin Islands National Park covers nearly two-thirds of the island. Renting kayaks on St. John is easy too, which is key since shipping three SUPs would have been prohibitively expensive, and getting them through customs damn near impossible.


It’s not even noon, but I take a huge swig. Besides toasting the successful rescue of Ted’s board from customs, the bottle of Cruzan Rum represents an appropriately Caribbean way to bless our departure from this wacky little town.


“No, no, we’ve got to do this right,” Ted says, snatching the rum. “We can’t drink it straight from the bottle. We gotta do bottle caps.”

Ted carefully pours a shot into the cap, the rum bulging above the rim. “This is a righteous elixir,” he says.

I shoot the cap.

“You need another one, Chief,” Ted informs me, handing over a second, and then a third, overflowing bottle cap.

This is how I know Ted and I are going to get along just fine.

Originally the expedition crew was to consist of myself, Robert Zaleski, C&K’s 30-year-old staff photographer, and my friend Todd Bradley from Oahu, a former champion outrigger paddler and founder of SUP manufacturer C4 Waterman. We’d been planning the trip for months, but our schedules never meshed so in his stead Todd offered up 49-year-old Ted Rutherford, C4’s mainland operations director and a part-time airline pilot from San Diego.

Circling St John


“You’ll get along great with Ted,” he assured me. “He flies for American now but he flew F-14 Tomcats for years. His call sign was Wacko.”

By mid-afternoon the heavily touristed and most populated west end of St. John is well behind us. We’ve passed five-star resorts, honeymoon villas, and multi-million dollar homes nestled in the trees. As we paddle past one particularly lavish estate, a pair of armed guards appear on the roof. I give them a little wave, which seems to take them off guard.

As we round Hawksnest Point, Ted sees something on the horizon and starts stroking. It’s Johnson’s Reef—a shallow patch of coral about three-quarters of a mile offshore where swells consistently break. Soon Ted is battening down his drybag and attaching his ankle leash in preparation for his first surf of the trip. This is another rationale for bringing along a standup board. You can ride waves on a sit-on-top, like the Wilderness Systems Tarpons Robert and I are paddling, but SUPs are made to surf.

Sensing a photo op, Robert moves his kayak closer for a better angle. He grew up surfing in New Jersey, so after watching a couple sets roll through he picks a seemingly safe spot to unpack his $5,000 camera. Soon the swell rears up and Ted takes off on a shoulder-high peeler, sailing majestically down the face before crashing spectacularly in the whitewater. That’s when Robert takes his eye from the viewfinder and sees an even bigger wave bearing down. He’s still fumbling with the waterproof case as I sprint for the shoulder and punch over the wave.


Circling St John


I watch as the bright orange bow of Robert’s kayak lifts up and out of the wave. Then the boat spins sideways and—WHAM—it’s a yard sale. Robert and his gear—sun hat, paddle, gallon jug of water, a plastic grocery bag of apples and oranges, assorted drybags, and the camera case, closed in the nick of time—are bobbing about.

“You know what, you got some serious style points out there today, buddy,” Ted tells Robert later over dinner at Maho Bay.

“That one snuck up on me guys,” he says.


With seven miles under our belts and the pre-trip jitters gone, we laugh about the carnage over Red Stripes and plates of green curry shrimp and coconut rice. It’s Asian night at Maho Bay Camps, a funky summer camp-style property with permanent tents connected by raised walkways snaking through the trees of a beautiful crescent bay.

After dinner, we crack our fortune cookies and read aloud the fortunes hidden inside. Ted’s seems particularly foreboding:
“You’re in for a big surprise soon.”
The surprise arrives the next morning in the form of a powerful weather front. As we round Mary Point just a mile out of Maho, the sky begins to spit rain, and the palms along the ridgeline lean sideways in the gathering gale. A headwind, naturally.


It’s a tough grind in the kayaks, and far worse for Ted, whose upright body acts like a sail. He leans deeply into the wind with every stroke, the force of the weather seeming to support him at an unnatural angle. It gets worse as we enter the larger, mile-wide Sir Francis Drake Channel, separating St. John from Tortola in the British Virgin Islands. Now the wind is stronger—gusting to 25 knots, with a stiff current ripping against us from the east.


At first Ted looks a bit deflated—you could hardly pick a worse craft than an SUP for a long upwind slog—and I worry that he will throw in the towel. But then his expression takes on a new focus, his strokes become more resolute and I feel guilty for even thinking he might give up. Former fighter pilots, especially those called “Wacko,” are not the quitting type.


In the distance, a cruise ship lazily pulls into port on Tortola and sailboats dash gloriously downwind, spinnakers flying. We press on grimly. After two hours of hard, uninterrupted paddling we slip into the shelter of Waterlemon Bay, just two miles from Mary Point. My sunglasses are so caked with sea salt that I’m oblivious to the fact that the French Canadian woman calling to me from a moored yacht is both topless and bottomless.

“Turtles!” she shouts in a garbled Franco-English that sounds more like Tah-toolls to me.
“What?” I ask.
“Turtles!”
“I’m sorry I don’t understand.”
“Turtles!” she yells again, exasperated. “There are turtles in the water.”
By the time Ted catches up, she’s no longer bottomless and the turtles are long gone. When Robert arrives, the show’s over.
“I think it’s time for a bottle cap,” I say, digging the rum out of my bow hold.
“After that?” says Ted. “Absolutely.”


We’re relaxing on the sand when, seemingly out of nowhere, tourists start arriving in groups of five and six to snorkel the Cay and visit the nearby Annaberg Sugar Mill ruins. We weigh the annoyances of the weather versus those of our fellow tourists, and shove off. We paddle back into the Drake Channel, where the contrary wind and currents have grown even stronger.


“It’s like a funnel in here,” Ted shouts above the whistling trades. “These are the heaviest winds I’ve ever paddled into.” He soon stows his paddle and resorts to stroking on his stomach. Though he’s making better headway, after 40 minutes of prone paddling he is in obvious pain.

“Wanna switch, bro?” I ask.
“Yes,” he says with zero hesitation.


All trip long I’ve been jealous of Ted and his SUP, but the Force 6 headwind cures my board-envy in less than 30 seconds. It’s painfully obvious that these boards are better suited for downwind runs and surfing than circumnavigating islands. Still, I embrace the challenge, put my head down, and just paddle. All day. The others are well behind me and sunset is less than two hours away when I reach Haulover Bay, so named because sailors used to haul their boats across the narrow spit of land into Round Bay—thereby avoiding the seven-mile upwind beat around the Point. Our destination, Vie’s Campground, lies less than a mile from the other end of the short portage those sailors blazed long ago. The Park Service prohibits camping anywhere on this side of the island except Vie’s, so there’s no middle ground. We either buck up for the seven-mile epic, or take the shortcut and surrender our—or rather my—plan to complete a full circumnavigation of the island. I’m busy scheming ways we can still make it around the Point when Ted and Robert join me on the cobblestone beach at Haulover. It’s too late to make the push around the East End, and Ted and Robert are clearly in no mood to commando camp halfway. We carry our gear past cactus and scrub brush to the placid blue waters of Round Bay. It’s like another world. Warm, sunny and totally shielded from the winds that made our progress so difficult on the other side. An hour later we’re sitting at Vie’s Snack Shack feasting on fried chicken, sweet Johnny cakes, and ice cold Red Stripes, and life seems pretty damn fine.


In the spirit of traveling ultra-light—and since we planned to mostly stay at hotels—I convinced the guys to leave their tents and sleeping bags in Cruz Bay. “It’s only one night,” I reasoned. “I mean, how bad could it be?” Just before sunset, we scavenge three beach chairs and place them under a wooden lean-to in preparation for the impending rainstorm.
“That was probably one of the worst night’s of sleep I’ve ever had,” Ted exclaims the next morning, sniffling from a new cold.
“That really sucked,” echoes Rob.


Circling St John

“When I woke up I was like, ‘Thank you, Jesus. Another day,’” says Ted.

The shelter where we assembled our makeshift camp was near a stand of tall bushes harboring lar ge populations of mosquitoes and no-see-ums, which attacked the boys unceasingly from all angles—even taking advantage of the elevated chaise lounges to sting them from below. Fortunately I had stayed up drinking with some new friends, and crashed in the sand under an old wooden table near the water’s edge. I actually slept pretty well.

“I need coffee,” says Ted.
“And a real breakfast,” demands Robert.

After a three-mile breakfast detour to Coral Bay, the crew is happily refueled and approaching Ram Head, a narrow point on the south side of the island known for rough currents, dangerous submerged rocks and a mass suicide almost 300 years ago.

Danish colonists came to St. John in 1717, importing legions of enslaved Africans to work vast fields of sugar cane, tobacco and cotton. In 1733 the slaves rebelled, seizing control of the island for six months until troops arrived from Martinique to restore order. Facing capture and the prospect of torture (the planters had instituted a slave code detailing barbaric punishments for rebellious slaves) some 300 people are said to have leapt to their deaths from the cliffs at Ram Head.

The rocky point stands as a somber reminder of that terrible day, and also marks a turning point in our journey. As we round the peninsula, the current from the Flanagan Passage barrels into the wide-open Caribbean, creating a turbulent sea. Waves explode on the rocks and a confused swell swats at our sterns, threatening to flip us. Then, as we arc west, the swell and winds are finally at our backs. Robert and I catch the occasional surf in our kayaks while Ted, with his body acting as a sail, is pushed effortlessly down the coast. We’d paid our dues—two days into the teeth of the Caribbean trades. Now it’s time to collect our reward. Ted surfs ahead, hooting with joy.

Circling St John

Later we rest at Saltpond Bay, snorkeling a particularly lively reef that could’ve been the set for Finding Nemo. That night we stay at the Virgin Islands Environmental Resource Station (VIERS), an educational and research facility deep inside the National Park which hosts student groups and—occasionally—ecotourists. “We just don’t get a lot of people on this side of the island,” VIERS executive director Randy Brown explains to us over a dinner of steaming lasagna.

We tell him that isolation is one reason we made the effort to explore St. John’s seemingly endless string of unspoiled cays and bays. The next morning reveals another: a waist-high wave at Reef Bay, two miles west of the research station. The waves peel one after another with machine-like perfection.

“This feels so good!” announces Robert like some surf-stoked kid as he slides along the swell in his kayak. I follow suit in my boat, and it does feel good. But as I watch Ted take off on a glassy little wave, do a smooth bottom turn and then trim effortlessly along its face, my SUP-envy returns. Thankfully Ted is in a sharing mood so Robert and I both take turns surfing his board.

Later we head ashore to explore the ruins of the Reef Bay Sugar Mill and hike to petroglyphs carved into a waterfall by the Taino Indians who came to the island as early as 300 B.C., island-hopping from South America in dugout canoes.

On the trail we pass the first people we’ve seen all day—a 40-something tourist in a pink polo shirt, leather topsiders and no socks. On his arm is his very well-put-together wife.

“What’s in the boxes?” he asks, gesturing to the Pelican cases of camera gear we’re carrying.
“Human heart,” I say coyly.
As they pass, I catch a whiff of her perfume, a flowery scent I can’t quite place. Once they’re out of earshot I say, “Wow, she smelled great.”
“Yeah, she really did,” agrees Robert.
Down the path, I’m quite sure the man and his wife are exchanging comments about the way we smell.

The woman checking us into the Westin St. John Resort must surely have noticed as well, though her training allows her to maintain a straight face and polite demeanor. We land on the luxury hotel’s white sand beach just ahead of a private ferry packed with tourists straight from the airport in St. Thomas.

Like a scene out of Fantasy Island, a hotel waiter hands frozen rum drinks to the guests as they disembark. I slip into the parade of pasty-faced mainlanders and suppress a smug grin. I can’t help but feel we’re somehow more deserving of the luxury we’re about to enjoy here at the Westin. We weren’t simply deposited here by some ferry. We worked for it. And we saw nearly every mile of St. John’s pristine coastline along the way. Places none of these tourists will ever see. Places the Island’s locals may never even visit.

As I swoop in and grab three rum drinks, the waiter eyes me suspiciously.
“My friends are over there checking in,” I feel compelled to explain.
Delivering the drinks to Robert and Ted, we hoist a toast. With just two easy miles left for the morning to complete our journey to Cruz Bay, we decide it’s time for a celebration.

Later, after a huge meal of fresh seafood and salads, we head back to our cushy two-story suite, our heads buzzing from too much sweet Cruzan Rum. As soon as I lay down on my bed, the telephone rings annoyingly.

“Hello?” I answer.
“Hello, Mr. Anders. I see here that you’ll be checking out tomorrow morning,” says the man at the front desk.
“Uh-huh.”
“Will you be needing a reservation for our private ferry back to St. Thomas?” he asks.
“No thanks,” I answer with a proud smirk he could undoubtedly hear in my voice. “We’ve got our own boats.”

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