
Air Mail
Sherpas to the Jet Set
By Mark Ellwood
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Malibu-based Cari Gray of adventure specialist Gray & Co. offers the same white-glove service. When she plots biking trips and similar expeditions for her clients, members of her team will test-run the route themselves—often twice—so they can anticipate every possible snafu. She anticipates elite travelers’ restrictions, too. Many C-suite executives, for instance, are not insured to travel on single-engine Robinson helicopters, which are commonplace in far-flung destinations. Gray will either bring in a new helicopter that satisfies the insurance requirements, or have a waiver ready for the adventuresome billionaire to sign.

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Late in 30 Rock’s run, Liz Lemon is confronted with the fact that her gig as a comedy writer might not last forever. After one stinging rejection, she’s wandering disconsolately down a gritty New York street when she hears a voice in the distance. “You are one of us now,” says the woman as she emerges, backlit, from a smoke-wreathed alley with two men flanking her.
When Liz asks who she is, the woman replies, “Better to ask who we used to be—people whose professions are no longer a thing.” One man is an American autoworker; the other used to play saxophone solos in rock ’n’ roll songs. “I was called ‘travel agent,’” the woman warns, inviting Liz Lemon to join their band of outcasts. “We live under the subways with the C.E.O. of Friendster.”
That was in 2011. Fifteen years later, however, travel agents have staged a comeback that even Demi Moore would envy. Last year, LinkedIn’s annual ranking of need-to-know roles, Jobs on the Rise, placed travel agent—or “travel specialist,” the preferred term these days—fifth on its list of hottest professions. Driving the revival are travelers with the deepest pockets: luxury travel is growing at around 6 percent annually, according to McKinsey, two percentage points faster than the industry as a whole.
“A travel agent is someone you don’t know you needed until you do,” says Jason Squatriglia, the New York–based founder of Your Favorite Travel Agent. He organizes six-figure-plus trips and has become a go-to fixer for the 0.1 percent. Want an impossible-to-score dinner reservation in a certain city? He can call in that favor for you. Fancy attending the Cannes Film Festival? He has scored tickets for clients through the luxury brands with whom he’s a major customer. “I connected the dots,” he says.
As he did when a client called him in a panic after a quick trip to Singapore, where she’d accidentally left behind her jewelry box while staying at the Marina Bay Sands. Squatriglia leapt into action, calling the hotel and booking the room for another two nights so there was no danger of another guest stumbling upon the valuables. Then he jumped on a plane, retrieved the jewelry, and hand-delivered it to her home in California. “They tipped me $5,000, which was nice, but it really wasn’t a bother for me,” he says.
Malibu-based Cari Gray of adventure specialist Gray & Co. offers the same white-glove service. When she plots biking trips and similar expeditions for her clients, members of her team will test-run the route themselves—often twice—so they can anticipate every possible snafu. She anticipates elite travelers’ restrictions, too. Many C-suite executives, for instance, are not insured to travel on single-engine Robinson helicopters, which are commonplace in far-flung destinations. Gray will either bring in a new helicopter that satisfies the insurance requirements, or have a waiver ready for the adventuresome billionaire to sign.
There is a simple litmus test for identifying a savvy specialist, she says, and it involves smoothing bumpy arrivals, especially after eastbound red-eyes. “Without being asked, we book the night before, very frequently,” she says. “It doesn’t matter how much money you have; at highly sought-after properties, you’re not getting in before four p.m. But if money is no object, your agent should have booked the night prior.”
Increasingly, high-end specialists such as Gray help with world-building, not just globe-trotting. Kevin Jackson runs San Diego–based EXP Journeys, which has carved out a niche in fantastical voyages. Take the day-long scavenger hunt around Rome he staged for one family, at a cost of around $80,000. They began with a private view of the Vatican, then raced around the city meeting actors dressed as different characters at landmarks such as the Pantheon and the Trevi Fountain. Each provided clues to the next location, culminating in a quest for Bacchus, the god of wine and revelry—or, rather, a party to celebrate their success, complete with musicians and dancers.
On another occasion, a father wanted to whisk his 13-year-old daughter away on a whirlwind tour of America’s national parks. His brief was straightforward but exacting: “I don’t want to see anybody, and I want to see the parks differently than anyone has ever done before.” Jackson devised a kind of private time machine: a Bell 429 helicopter that allowed father and daughter to touch down in remote, untrafficked corners of eight parks in five days while meeting actors playing historical figures associated with a particular locations, from Theodore Roosevelt to John Wesley Powell. “Each day a character would give them a clue to unlock the next day’s experience,” says Jackson.
Connections, cachet, and theater are all very well. But the strongest argument for the rebirth of the travel agent arrives when travel itself goes wrong. Paul Tumpowsky, the founder of Fora Travel, says that when Gulf airspace shut down at the start of the Iran war, he was handling 75 percent more bookings than usual. Tumpowsky doesn’t just have a hotline to airline executives who can intervene when problems arise; he has an offshore team that can spend hours on hold with airline help desks so the agency’s clients don’t have to. When an agent finally answers, the team can resolve multiple re-bookings in a single call. Compare that with the passengers venting on social media about spending hours trying to reach Qatar Airways and other carriers while stranded with little reliable information.
A similar scramble followed the rendition of Nicolás Maduro in January, when Caribbean airspace closed during one of the busiest travel weekends of the year. Tumpowsky had clients stranded on St. Barth’s after their Saturday flight was canceled and spent hours hunting down four seats to get them home. “Trump has an affinity for doing these things on a Friday night at Mar-a-Lago,” he says. “So on Saturday morning, we wake up to a whole new world, and spend the weekend on processes and procedures.”
Squatriglia had clients who were caught in that same mess. He took a more expensive route. As soon as he learned the airspace had been closed, he began watching for private aviation slots to reopen. A major client of VistaJet, he was able to secure one of them and charter a plane from St. Maarten to Miami, albeit at a 40 percent premium over typical rates. “We sold it by the seat to get people out of St. Barth’s,” he says. “My goal is to never tell anybody no.”
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