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Hilton Is Whisking Strangers Away to Mystery Destinations. Here’s the Business Lesson Behind It.

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Hilton Is Whisking Strangers Away to Mystery Destinations. Here’s the Business Lesson Behind It.

Hilton marketing executive Dan Reynolds and comedian Heather McMahan explain what travelers are truly craving, and what any business can learn from listening closely to its customers.

As someone who is allergic to planning, I wasn’t totally shocked to learn that research by Hilton and Morning Consult reveals that 79% of U.S. adults would drop everything to take an all-expenses-paid mystery trip. And their 2027 Trends Report also reveals that 41% of travelers plan to take a solo trip in the next year, with relaxing and recharging as the number one goal. Again, something I can fully relate to.

Those stats became the basis for Hilton’s Whisk Away sweepstakes, part of their New Ways to Stay campaign: six winners get a mystery solo getaway to a surprise destination. To celebrate the giveaway, Hilton set up a pop-up in New York’s Times Square on the doorstep of the Nasdaq MarketSite, where Hilton rang the opening bell.

I attended the event (where I sadly didn’t win a free mystery trip, but did get some tasty cookies) and spoke about the sweepstakes and travel trends with Dan Reynolds, Hilton’s SVP of Global Marketing, and comedian Heather McMahan, whose globe-hopping tours have taught her a thing or two about the benefits of putting a little adventure and luxury in our lives.

Heather, what do you think it says that so many people are like, “I don’t care where we go — just throw me on a plane and get me out of here”?


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