LAST FEBRUARY, Morgan Callagy found himself a very long way from his home and office, which was precisely where he wanted to be. After a day heli-skiing in untouched powder in the Italian Alps, the London-based general partner at private-equity firm Veronis Suhler Stevenson and 9 of his closest male friends had crossed the border to Val d’Isère, France. There, at La Folie Douce—an après-ski bacchanal where neon-costumed revelers dance to Europop and drink Jägermeister shots served on wooden skis—Mr. Callagy and his crew boogied on the rafters in vintage Bogner ski suits and blond mullet wigs.
Enough diversion? Not at all. After the sun went down, the guys swapped their wigs for headlamps and snow shoes and trudged a mile through the woods with their guides to an abandoned mountain farmhouse, where they sat on pointedly rugged animal skins around a candlelit table and ate a meal of côte de boeuf cooked on an open fire and washed down with multiple rounds of Génépi, a potent herbal liqueur. “For those few hours, we got to forget all about the real world,” Mr. Callagy said. “It was one of the most memorable days of my life.”
A 44-year-old father of three, Mr. Callagy is a member of the growing ranks of men traveling with groups of male friends on testosterone-rich trips variously dubbed guy getaways or bro-cations. These often over-the-top adventures are opportunities to bond, blow off steam and, in the age of Facebook and Instagram, digitally boast a bit. “Today’s type-A male traveler needs more than a shady palm tree and swim-up bar,” said Owen Gaddis, a luxury travel manager with custom tour operator Absolute Travel. “They crave constant engagement in their leisure time as much as they do in the workplace,” Mr. Gaddis said.
Eleven Experience, which manages a collection of six fully staffed luxury lodges from Colorado to the Bahamas, is one of several companies that have sprung up recently to meet hard-charging types’ growing appetite for trips that both push the boundaries of luxury and push them out of their comfort zones. The company charges $31,500 to $128,625 a week for its properties, including the price of its skiing and fishing guides.
Mr. Callagy, a self-described Eleven junkie, has been to all of the company’s properties. “My friends and I refer to Eleven as man-camp meets Neverland.v Experiencing something unique and challenging with friends is what these trips are all about. My life would feel incomplete without them,” he said.
Other travel companies catering to groups of adrenaline-infused men include the U.K.-based Secret Compass, which takes clients white water rafting in South Sudan and mountain biking in Afghanistan, and White Desert, which specializes in Antarctic glamping trips, complete with a slightly shivery Champagne lunch and the opportunity to sauna at the Russian research station. Though it would be easy to dismiss these trips as stereotypical manifestations of the Peter Pan complex or stunts for alpha males looking to push their limits in the wild, the men who take them say that it goes deeper than that. Charles Field-Marsham, a Toronto-based entrepreneur, has taken ski trips with the same five guy friends for the past decade. “It sounds corny, but meaningful relationships keep you happy in life and one of the best ways for men to build meaningful relationships is through travel and sports,” said the 47-year-old father of three.
Howard Chudacoff, a professor of urban studies at Brown University and author of “The Age of the Bachelor,” said that historically the saloon, pool hall and barber shop served as male retreats where men “could joke and swear and complain about relationships or jobs and find the support they didn’t necessarily get in their family life.” Today, Mr. Chudacoff, said, traveling together to chase some physical high has taken the place of communing in those low-risk sanctums
Having skied throughout North America, Mr. Field-Marsham and his group were looking to raise their game. “We wanted to be pushed physically, but also wanted luxury,” he said. He reached out to Danielle Stynes, founder of Swisskisafari. For a minimum of $1,000 a day per person, Ms. Stynes creates what she describes as a James Bond holiday. “My trips appeal to men who have it all and who think they have done it all,” she said. To deliver what she promises, she employs helicopter pilots, ski guides and an avalanche expert who has a doctorate in snow forecasting.
Ms. Stynes said that 90% of her business is guy groups. “They’re fit and competitive and really want to feel like they’ve earned the end-of-day wine and gourmet meal,” she said. Mr. Field-Marsham said a highlight of his group’s trip was skinning (climbing uphill on skis) two hours to Switzerland’s 1,000-year-old St. Bernard monastery, where they lunched with monks before spending the rest of the day skiing downhill. “That’s an experience my friends and I will talk about for the rest of our lives,” he said.a.
Glenn Mason, a vice president of sales with United Parcel Service, Inc. in Atlanta, and his group of 20 cycling friends buy out Hotel Domestique, a luxury property in South Carolina’s Blue Ridge Mountains, for a long weekend each summer. The hotel caters to hard-core riders who want to pedal from morning to noon, then lounge by the pool and dine on upscale grub like Wagyu flat iron steak. Each time they visit, Mr. Mason and his group tackle a brutal 100-mile ride. “Halfway in there’s a 1.5-mile stretch that has inclines of 22 to 28%,” he said. “It beats us up, but completing the 100 miles together creates a special bond.”
Andrea Mason, his wife of 28 years, said she welcomes Mr. Mason’s annual trip because he’s increasingly animated as it nears and returns energized. “Some people might see it as selfish to go away without your spouse, but it’s good for our marriage,” she said. “I wouldn’t want to tag along and ride 100 miles. And when Glenn’s away it’s my time to relax.” She said that she takes advantage of his absence by dining out more with friends.
Michelle Sharpes, whose husband, Brian, the managing director of investments for UBS in San Francisco, takes four ski trips with a group of 10 guys each winter, also sees an upside to his regular disappearances. “We get so wrapped up in our roles as husband, wife, father and mother,” she said. “A few days to step out of those roles and just be Brian or Michelle is really important.”
Norman Howe, president of the active travel company Butterfield & Robinson, said he’s seen such an rise in demand for guy-getaways that he’s considering tailoring itineraries specifically to groups of men. “The first thing men do when they go away together is stop shaving,” he said. “It’s a primal expression of their freedom from authority and constraints.”
Men who want to give their primal side an especially brisk workout might consider traveling to Indonesia’s remote Sumba Island. Though headhunting has thankfully been banned there, travelers can still go into the jungle with villagers to spear hunt wild boar. “It’s a very macho, chest-thumping society,” said Carla Petzold-Beck, general manager of Nihiwatu, a five-star eco-resort on the island that is popular with surfers.
Even men with no particular affinity for Vladimir Putin-style machismo find benefits in guy getaways. “There’s something about being outside in the middle of nowhere with guys that is very different from being on a tennis court or golf course,” says Hal Schroeder, the president of Concept Services, an Austin-based company that sells food-service equipment to restaurant chains.
Mr. Schroeder and a group of male friends make annual pilgrimages to Guayacaste, a dove-hunting lodge in Argentina, and to Nimmo Bay, a heli-fishing lodge in British Columbia. He describes himself as a mildly enthusiastic hunter and fisherman. “That’s not really the point,” he said. “The point is escaping to a place where you can just be a guy. That doesn’t mean acting crude, but just not having to deal with responsibilities or routines. There’s the saying, ‘boys will be boys.’ If you let us be boys once in a while, we’ll be better men for it.”
He was so smitten when he visited Nimmo Bay 15 years ago that he told the owner to sign him up for the same week every year for the rest of his life. He visits with around eight friends, most of them tennis buddies. “We land on a remote glacier for cocktails chilled with glacial ice and a lunch served with silverware and linen napkins. The staff snuggle you up with warm blankets and you have the fire going and might get to see a grizzly bear attack something. It’s really like the wild kingdom.”
Mr. Schroeder admits he could probably forgo glacial-ice martinis and just go camping, rather than spend $150,000 to buy out a lodge for a week. But, he said, life is about collecting rich experiences. “When you’re successful, material things are easy. Experiences are what you take with you.”
1878-79 | A 21-year-old Theodore Roosevelt goes camping in Maine along with William Wingate Sewall and Wilmot Dow, on one of the first of Teddy’s countless guy trips.
1904 | A group of avid outdoorsmen founds the Explorers Club to “unite explorers in the bonds of good fellowship.” Honorary members include Walter Cronkite and John Glenn. Women were admitted in 1981.
1918 | Henry Ford, Thomas Edison, John Burroughs and Harvey Firestone—who dubbed themselves the “Vagabonds”—take the first of many summer trips together.
1940s | Gary Cooper and Ernest Hemingway’s bromance begins with a pheasant-hunting trip in Idaho.
1960s | Dean Martin, Frank Sinatra, Sammy Davis Jr., Peter Lawford and Joey Bishop ricochet between Miami, Las Vegas and Palm Springs on a red-blooded hunt for hedonism and handmade suits.
2004 | Looking to test their endurance and get a fresh perspective on the world, actor Ewan McGregor and adventurer Charley Boorman take a 20,000-mile, 12-country motorcycle trip from London to New York City.
2015 | President Obama hangs out in the wilds of Alaska with adventurer Bear Grylls, drinking tea made from catkins and eating salmon picked over by a (real) bear.