Forget Your Chalet. The Ultimate Ski Trip Flex Is Booking With a Top Instructor.
In Aspen, ski pros began fielding requests for lessons for the upcoming winter season early in the summer. There are 1,350 pros in the famously-moneyed mountain town and the best were long ago booked, says Jonathan Ballou of the Aspen Skiing Company, the area’s premiere ski school. Forget Olympians, scoring a booking with even a ski bum instructor during peak period, from Christmas through New Year’s, has been impossible for months.
It’s a similar story in Deer Valley, the exclusive skiers-only resort in Park City, Utah, where private full-day lessons are $1,490 during high season. Reservations with its 600 instructors opened after Independence Day, and they’re booked solid. Kurt Hammel, a manager at the ski school, says Deer Valley has one of the highest percentages anywhere of people taking ski school lessons on peak days.
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Over the last five years, a barrage of luxury resort brands like One&Only and Montage have planted flags in coveted ski destinations, creating more high-caliber rooms for more uncompromising personalities. Every one of those guests wants a top ski instructor, and booking them has turned into a high-stakes competition to better the best.
“While I don’t have any hard evidence of this happening, I guarantee the reservation desks are offered bribes regularly by repeat guests who will try to go the extra mile to book the instructor of their choice,” Dan Sherman, CMO of Ski.com. “I also know that sometimes a skier may go around the ski school directly to their instructor and offer a premium if the instructor clears their calendar. However, since all lessons on the mountain must be booked through and sanctioned by the resort, partaking in this type of booking would result in the termination of the ski instructor.”
While it happens, the top 1 percent of instructors are like Ivy League universities—they value legacy over flash cash.
“[Returning guests] end up with the same instructor,” Hammel says, noting that those connections often go back for many years. Ballou adds that it’s not unusual for the top, veteran pros in Aspen to ski with three or four generations of a single family.
Joining that club isn’t easy. It takes patience, planning, and a lot of full day private lessons, says Brenna Kelleher, a pro who has been with Big Sky Resort for 15 years. There, private instruction starts at $1,195 and rises depending on the date. Kelleher estimates that all but three of her lessons last year were private client requests—and she taught over a hundred. Most of those clients were returning guests from previous years.
“People lock me in for certain dates and then I’m locked in,” Kelleher says, adding that skiers wanting to book with her can go through the ski school, but it’ll be a “labor-intensive thing,” and not one she recommends. The key is year-after-year loyalty and multi-day private bookings, she says.
While Kelleher isn’t accepting offers from the highest bidders, she emphasizes that generous tips are also key—especially given that instructors (at Big Sky and elsewhere) don’t see even half of what you’re paying for a full day of instruction.
Tracy (T-Bone) Taylor is one of the Colorado resort’s most beloved and in demand instructors. He’s taught at Telluride’s Telluride Ski & Snowboard School since 1988, and counts names like country star Dierks Bentley as clients.
Every day his phone buzzes with an avalanche of direct booking requests—but the ones that win out showed “financial recognition,” he says.
He recalls a client that struggled to find an available instructor for one of his less-advanced kids. “He wasn’t a very good tipper,” says Taylor, who had to gently explain to the guest why he was being blackballed.
But relationship building with an instructor often goes way beyond a Venmo salute or a midday meal (clients typically foot the bill for a nice on-mountain lunch). For instance, one of Taylor’s clients values the veteran instructor so much that he has invited him on ski trips in Canada and—paying his way and compensating him for his time and effort on the mountain.
It’s a process that creates “deep and meaningful connections” between teacher and student, says Ballou.
“What people are buying is a personal concierge that’s also an expert,” he says. “They’re buying time with a companion.”
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