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Meet the Fearless Travel Planner Creating One-Off Adventures for High-End Clients

Henry Cookson takes us to Colombia to experience the thrills firsthand.

Henry Cookson paraglides down toward a riverbed, where a helicopter awaits to explore Chicamocha Canyon. Christopher Bagley

It’s not often you’ll see Henry Cookson gasping for air, but right now he’s huffing and puffing as he stands at the edge of the 400-foot Hoyo del Aire sinkhole in the highlands of northeastern Colombia. The burly Brit adventurer has just rappelled to the bottom of the crater to explore its overgrown floor before pulling himself back up his climbing rope in midair, one grueling tug at a time. We’re north of Bogotá in a remote part of Santander province, where the Hoyo is one of many natural marvels that come with not only dozens of rare bird and plant species but also dramatic backstories—some darker than others. Locals say that only about 80 climbers have ever made it down to the base of the sinkhole and back, though over the centuries plenty more have been pushed over the precipice to their deaths, either by Spanish conquistadors or modern-day guerrillas or paramilitaries. Sure enough, Cookson reports that one of his first sightings amid the thick vegetation below was a human shinbone sticking out of a corroded combat boot.

But Cookson isn’t one to be deterred by a little gore. Instead, he’s pondering how he might manage to lower his clients into this spectacular crater in a more pleasant—and less hair-raising—way. To start, next time he’ll bring a tent. “Imagine being at the bottom of this ancient hole in the ground and looking up at the stars,” he says. “About 5,000 people have now climbed Mount Everest, but only a handful of people have ever seen this amazing place.”

By now it’s probably clear that Cookson isn’t your average travel planner. A well-connected Londoner whose past lives range from African safari guide to Goldman Sachs banker, he’s remarkably comfortable dangling from a thin rope a few hundred feet in the air. He’s also a seasoned expert at putting together extreme itineraries for his clients at Cookson Adventures, one of the world’s most exclusive travel companies. In an industry in which everyone seems to be selling bespoke experiences with varying degrees of legitimacy, Cookson is the real deal, producing one-of-a-kind adventures—exploring Antarctica via private submarine, saving giant tortoises in the Galápagos, scaling volcanoes in Nicaragua—that can cost well into the six and even seven figures, a chunk of which is often directed to nonprofit conservation efforts. So when he asked Robb Report to join him on his first Colombia scouting trip, helicoptering around some of the country’s least-visited regions to test the possibilities for everything from paragliding to giant anteater tracking, we cleared our schedule within about 10 minutes.

Barefoot llanero cowboys lasso a wild horse that they’ve herded into a corral on a ranch near Corocora Camp

Barefoot llanero cowboys lasso a wild horse that they’ve herded into a corral on a ranch near Corocora Camp.  Christopher Bagley

Cookson’s Colombia lies in terra incognita, away from established hot spots like Cartagena and Medellín and in regions that, until recently, were the territory of camo-clad revolutionaries. Although the country is now safer than it’s been in decades, some of its more isolated regions, like Los Llanos wetlands in the east, remained off-limits for so long that they’re still largely unvisited, even by Colombians. It is in this tropical savannah, the land of the fabled llanero cowboys, that we begin our trip, checking into the new Corocora Camp, which is set on a private 22,000-acre reserve inhabited by river-dwelling caiman crocodiles and clusters of capybaras, the native mammal that looks like a giant guinea pig.

At Corocora we make like llaneros, wandering on horseback through the Edenic region of big skies and palm-studded lagoons, where, judging by the chorus of chirps, the parakeet-per-capita ratio must be somewhere near 1,000 to 1. Apart from the nonstop sightings of scarlet ibises and Orinoco geese (Colombia is home to 1,800 bird species, more than any other country in the world), the biggest surprise in Los Llanos is our immersion in the traditional local culture, where lone cowboys ride barefoot while herding cattle and even while taming wild horses—a brutal and bloody but totally spellbinding ritual that we witness from right inside the corral at a ranch near Corocora.

A staffer at Corocora in Colombia prepares the main tent for a meal.

A staffer at Corocora prepares the main tent for a meal.  Christopher Bagley

But the llaneros have a gentler side, too. One evening a local group of musicians arrives at Corocora on motorbikes and sets up near the main tent, where cuts of grass-fed beef are roasting over a bonfire. In the repertoire are wistful ballads like “Mi Tristeza” (translation: “my sadness”), in which an aging herder imagines the day he’ll be too old to take his horse across a river. Mesmerized, Cookson films every song on his iPhone, then trades Facebook contacts with the band members. He’s also not bashful the next morning when we encounter a giant anteater—notorious for its lethally sharp claws—nosing around in the bushes. Cookson creeps up to within a few yards of the remarkable creature for a degree of closeness he says is rarely possible in the wild. “Luckily, the giant anteater is basically blind and deaf,” he says. “And it has no natural predators here.”

One afternoon Cookson decides we should swap the serene comfort of Corocora for a $20-per-night hotel in the scruffy river town of Santa Rosalía, where pigs and roosters roam the main street—and where Cookson says we’ll be better positioned to spot the tonina, a rare pink river dolphin that’s become endangered here due to river contamination and illegal fishing. We arrive by propeller plane at night, then set out at 4:30 the next morning, coating ourselves in bug repellent before we board a motorized lancha for the trip up the caramel-hued Meta River. It’s not long before we spot a quick flash of rosy skin—a pair of frolicking dolphins. According to legend, the animals transform themselves into humans at night and come ashore to seduce young women.

Kogi tribesmen in a village in the Sierra Nevada de Santa Marta

Kogi tribesmen in a village in the Sierra Nevada de Santa Marta.  Christopher Bagley

The whole scene is a far cry from Cookson’s posh upbringing in England, where he attended the elite Harrow School and followed a typical path to a career in banking. All along, there were hints of the irreverent outdoorsman within: At his office at Goldman Sachs, he was known to walk around shoeless, much to the annoyance of his boss. And then there was the time in 2005, when, on a whim, he and two buddies entered the Polar Challenge, an annual 360-mile footrace to the North Pole. “We were competing against 17 other teams, including Marines who were Arctic warfare instructors,” Cookson recalls. “Everyone thought we were a joke.” But they finished in first place. Part of their strategy was to focus on tiny details that other teams overlooked. “If you’re cross-country skiing while dragging a sled behind you, you’re not going to be going that much quicker or slower than anyone else,” he says. A few clever modifications—e.g., bringing extra mini-stoves to melt snow faster and removing dried food from its packaging before departure to save valuable prep time— gave Cookson’s team the edge. Two years later they regrouped to snag a Guinness World Record for a 1,100-mile kite-skiing trek to the Southern Pole of Inaccessibility in Antarctica. For both achievements Cookson credits a combination of serious determination and impish lightheartedness—qualities that continue to define his business philosophy today.

Back in London, Cookson began arranging off-the-grid trips for friends, and in 2009 he officially launched Cookson Adventures. Pulling off the impossible became the company’s credo: When a client requested a guaranteed puma-sighting in Chilean Patagonia, Cookson hired an interior designer to redo a decrepit local farmhouse hundreds of miles from any other accommodation—but right in the middle of the animals’ natural habitat. For another client, he arranged a first descent in a river raft down a treacherous stretch of whitewater in Belize and, as a bonus, worked with a local archaeologist to visit a nearby cave with untouched Mayan ruins. Each of his made-to-order journeys can require several scouting missions and an extensive on-the-ground team, which is why the tab often reaches several hundred thousand dollars. “If money really were no object, most people could achieve most things,” Cookson says. “You could just throw cash at everything and bring in all kinds of advisers until you get it right. So it’s not just about having a large budget—it’s about how you allot it intelligently.”

Henry Cookson on a footbridge near the base of the Tisquizoque Windows waterfall in Colombia

Cookson on a footbridge near the base of the Tisquizoque Windows waterfall.  Christopher Bagley

Throughout our own trip Cookson devises complicated strategies for linking up all of Colombia’s esoteric highlights for his seen-it-all clients. He concludes the best way to see the mile-deep Chicamocha Canyon—the world’s second-deepest gorge—is to paraglide down to an accessible entry point and then board a waiting helicopter, which has us zigging and zagging right through the canyon’s most spectacular and least visited section (a move that would surely land us in jail in a more touristy destination). He decides that there’s not one, but three ideal ways to view the otherworldly Tisquizoque waterfall: from the air via chopper, from the ground via 4×4 and, finally, after a long and slippery uphill hike, from within the massive limestone cave at its source, some 1,000 feet high. In the picturesque colonial village of Barichara, where most visitors would satisfy themselves with leisurely strolls along cobblestone streets, Cookson immediately zeroes in on a shop selling containers of the baked black ants that are a local specialty. Eating a handful of them is, of course, nonnegotiable. (Texture: crunchy. Flavor: ant-y.)

At a time when genuine one-of-a-kind experiences are increasingly difficult to find, Cookson is especially conscious of the ethical dilemmas posed by high-end travel. One of our most memorable outings of the week is a visit with the self-isolated, indigenous Kogi people in a cluster of thatched huts in the Sierra Nevada de Santa Marta, near the ancient ruins of Ciudad Perdida. Though the settlement is generally off-limits to outsiders, our encounter has been arranged by one of Cookson’s local fixers, and after some deliberation among the white-robed tribal elders, we are guided through the village.

Henry Cookson takes a dip by another waterfall near Tisquizoque in Colombia.

Cookson takes a dip by another waterfall near Tisquizoque.  Christopher Bagley

The Kogis—whose name means “jaguar” in their native tongue—have changed little since the days of the Spanish conquest, remaining fiercely resistant to such modern conveniences as electricity and plumbing, to say nothing of Instagram. One man sits with a deerskin drum and plays a traditional song that laments the damage that the “little brother” (white man) has inflicted on the planet. Before we leave, Cookson, clearly affected, stops to offer the elders a respectful thank you, noting how much we have to learn from the Kogis’ reverence for nature and commitment to their traditions.

The next night, as we sip sundowners on the terrace of a private villa nearby, Cookson wonders whether we should have visited the village at all. “It’s a tricky one,” he says. “These places can teach us so much. But every time we visit them with our cell phones and cameras, no matter how well intentioned we may be, we’re inevitably eroding their culture just a little bit.” He also feels a bit guilty about relying on noisy helicopters to reach some of the most pristine wilderness in South America, but his clients aren’t going to settle for bumpy 12-hour drives over terrible (or nonexistent) roads. And increasingly, Cookson is finding ways to weave in conservation or charity components to his trips, as more clients realize that meaningful experiences generally trump pure hedonism and bragging rights.

But when you’re traveling with Cookson, boast-worthy moments tend to occur naturally. One of his goals throughout the trip is to spot an anaconda, the giant python that’s native to the area. It seems we have a good chance in the middle of a lagoon one day in Los Llanos, as our horses clomp through swampy water that’s 5 feet deep. “Right now we’re probably surrounded by several creatures who would quite happily swallow a big crocodile,” Cookson observes a bit too gleefully. We never do spot one of the 25-foot snakes, and as we head back to Bogotá, I can’t help asking what Cookson would say to a customer who came all the way to Colombia and didn’t get to see an anaconda. He smiles. “If a client really wants to see one,” he says, “I’m pretty confident I could make it happen.”

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