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A Maldives Surfing Safari

A Manhattan mom, four teenagers and a former pro surfer named Wingnut go in search of epic waves in the Indian Ocean via the Four Seasons.

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As I straddle my surfboard just after dawn, a slight haze distorts the horizon off the Maldives break. I can’t measure the next set of waves until they are literally upon me, but visions of the eight-foot swell we endured the day before are fresh in my mind. I arch my shoulders and splash my legs to shake my nerves. If I wipe out, it’s just water. I inspect my feet dangling underwater off the sides of my surfboard; nothing but fleshy bait asking for that sharp-toothed crunch....

My first “surfari” to the outer reaches of the Maldives had been made all the more challenging (fear-inducing?) by the sighting of a hefty shark that very morning during a scuba dive with my daughter. The area is known to be safer on the shark front than most—just a few reef sharks and hammerheads that glide by, uninterested in the scent of humans. Still, it takes Zen-like concentration to ignore the imagined bass strings of that movie I need not mention. Duntah duntah duntah…

Fear is nothing but the stories we tell ourselves, I think. 

I lay down and start paddling toward the crystal blue swell breaking off the barren reef.

The Maldives is a narrow island nation formed by two sets of 26 atolls that create a chain with open water and crooked channels between them. The country sits in the Indian Ocean and the Arabian Sea, about 2,000 miles from the coast of Somalia—safe to say, in the middle of nowhere. Rising sea levels mean the low-laying country is literally sinking: all the more reason to plan the world’s greatest surfari—a world-class vacation complete with underwater wildlife sightings while hunting for the greatest waves on the planet—while I can.

My three kids (now 17, 15 and 11) and I picked up the sport about seven years ago in a surf camp on New York’s Long Island. My happiest parenting moments include the four of us paddling our nine-foot long boards like mad to drop into the same wave. As the sun set and we’d pile into my Jeep all salty and tired, we’d spend the evening hours arguing over who got the wave of the day.

At first I bested my children and helped them coast along the calmer Long Island summer surf. As everyone improved we started traveling for waves, surfing Costa Rica, Cabo San Lucas and Brazil. 

This summer my oldest, Chloe, and I were ready for bigger surf and dreamed of the Maldives’ huge yet relatively forgiving waves. (Warmer climates create waves of all heights, but they are more often glassy. Glassy is preferable in the same way any skater prefers a Zamboni-smoothed-out Olympic rink over knotty, leaf-strewn pond ice in the backyard.)

For years I’d heard the glorious surfer lore about the Four Seasons Explorer, a ten-stateroom, 129-foot catamaran managed by the hotel brand’s Kuda Huraa resort (see “The Details” below) that is often chartered by Australian-based company Tropicsurf and their world-class instructors. So one late afternoon last June, our motley crew, made up of a semi-terrified, possibly regretful mom, her daughter and three teenage boys arrived at the Maldivian capital of Malé after a 20-hour trip through Dubai. On the docks of the nearby Kuda Huraa hotel, the humid smells of tropical flowers and the ocean overpowered me as a small tender arrived to speed us across to the Explorer, seawater spraying our filthy travel clothes.

In the distance, the enormous white catamaran stood impossibly still on two stabilizing hulls. As we boarded we were handed fruit smoothies and magnolia-scented cold towels. The warm and very unstuffy staff winked at us with a twinkle in their eyes. Eight Australians, guests who had arrived earlier in the day, introduced themselves through smiles as wide as the Indian Ocean. One of them, an ex-Navy man named Chris (a B surfer in style but an A in drive), welcomed my teenage posse by teaching them how to safely jump into the water from the third deck before they’d even found their cabins. I opted instead to sip my fruity drink against the backdrop of a flaming orange sunset. Perhaps my regrets about taking these kids across the world to a floating hotel were unfounded.

After a dinner of locally caught grilled wahoo with lime and cilantro, barbecued honey ribs and shredded vegetable salad with raisins—all served as a casual buffet with tables set each night for two, four or ten (depending on our desire to mingle)—the 20 guests (only 12 will actually surf; the maximum Tropicsurf ever allows, in order to keep the line-up uncrowded) packed it in for a sunrise session off a distant island, a ten-hour sail away. 

The flexibility of surfing from a boat is unparalleled. From midnight to dawn, the steady catamaran tears through the black and sometimes angry sea, hopping from island to island in search of the best arrangement of wind and swell. Our ship powered through that first night to a famous break called Farms, its movements barely detected as we slept.

At daybreak we bounded upstairs, heaved open the white metal door and watched perfect, shoulder-high sets roll past the boat, breaking another 100 yards toward the sand. We were on our boards heading toward them less than ten minutes later.

Surfers dream about corduroy waves coming in a set of stripes over a calm ocean. When they did and they broke against the shallow reef beneath us, we could be sure the force of the wave was thrilling and more powerful than we’d ever felt. As we raced down the line, the white water chased after us like a pack of wild dogs. One day I fell into a wave smack on my back and not only got the wind knocked out of me but heard my spine crack from top to bottom. 

Tropicsurf guides work hard to encourage safety. A small army of their instructors were sent with clear marching orders: Addi would remain out in the line-up and give us an extra push into the powerful overhead waves if we needed assistance (Mom did, kids didn’t); Adam would wait in the white water 100 yards away to catch us and help guide us back out; and two more men stood guard on the tender in case a quick rescue was in order. 

I also brought our own personal coach, because I wanted a set of eagle eyes on our group only. Robert Weaver, known the world over as Wingnut, is a former pro surfer who starred as the long-boarder in the movie Endless Summer II and is now a regular guide for families on surf trips to unknown, potentially dangerous breaks. Wingnut surfs like a Globetrotter plays ball (“He’ll moon you as he’s surfing by, most likely in a handstand,” joked a friend before we left), but he’s there to keep us prudently aware of the power of the ocean. “Mostly, I just know when the surf is too big or too shallow and when you are too tired to be safe,” he says.

After a day sloshing in the sea, the kids and I, along with our new friends, would rest on the Explorer, where everything felt luxurious but never over-the-top silly, like so many of the boats in an August St. Tropez harbor. 
There was just enough space (215 square feet, to be exact) in the white and chocolate-brown staterooms to help us unwind privately. Bright blue lounge chairs on the ample-sized decks comforted our exhausted bodies, while overstuffed beige sofas in the living room sheltered us from the intense sun and doubled as a screening room to watch videos of our 
progress, filmed from the tender each day. Plus, the doting crew was always at the ready to deliver any kind of drink or snack. 

But it’s not only families and delightful Australians who frequent the Explorer. Each August, for the last four years, the Four Seasons Kuda Huraa has held the Four Seasons Maldives Surfing Champions Trophy, an invitation-only competition—called the “most luxurious surf contest in the world”—that pits former world champions against one another on various boards to see which pro from which era is best on all the different equipment. The invitations were out, and Four Seasons was awaiting replies while we were there. There was a buzz of excitement when word spread that Australian free-surfer Dave “Rasta” Rastovich and Brazil’s Fabio Gouveia had confirmed. 

“It’s pretty cool to see these modern legends do battle. They went head-to-head back in the day. Now they’re all friends but still hate to lose to each other,” says Wingnut, who often watches the event unfold while sipping piña coladas from the Explorer’s upper deck. (Rasta would later take home the top prize.) 

On those very same waves, for ten days our group tried its hardest to nail a good bottom turn and ride in a wave’s sweet spot from sunrise until the moon shone. It would take ten minutes to scrub the sunscreen and salt off our bodies, and each night I did so alone in the outdoor shower off the back stern sea-level ledge. Once, I slipped on the sudsy shampoo and barely missed falling in and being carried out to sea before anyone knew I was gone. That near-fatal slip showed that I could die in the shower well before an eight-foot crumbling wave drowns me or a Great White chomps me whole. All more fodder to quiet those fearsome stories that exist only in my head.

Was the madness of taking four teenagers across the planet worth it? Together we tore down the line in see-through waves while our hearts raced in unison. Each of us caught our own best wave, which we’ll replay forever in vivid detail as if we achieved it that very morning. To share that intense joy is the ultimate in human bonding, and a reason well worth this surfari adventure, for sure.


The Four Seasons Explorer arranges three-to-ten-day all-inclusive surfing itineraries on its three-deck catamaran, which accomodates 22 guests and a 25-member crew (from $6,000 for three nights). We also recommend spending several days before or after at either (or both!) of Four Seasons’ heavenly Maldives properties: Kuda Huraa, with its overwater bungalows and suites—we like the one-bedroom Water Suites (rooms, from $2,450)—and Landaa Giraavau (rooms, including bungalows and suites on stilts and beachside villas, from $1,600), hidden away on the pristine Bataa atoll.


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