Shoe mogul Stuart Weitzman does it. Instagram influencers are playing it to up their follower-game. And regular people are trying it to get out of their travel ruts. The rules are simple: Show up at the airport. Book the first flight you see. Leave.
Sure, there are practicalities to consider: How do you pack for a trip that could take you to Alaska or to Jamaica? And how do you book your hotel and your activities if you don’t know where you’re going until you leave?
So travel roulette has transformed into a business.
Jess and Kim Lawrence hired a travel roulette company for their honeymoon. Between owning a photography company and planning a wedding, the couple had no time to plan their honeymoon.
So they decided to play travel roulette.
They contacted Whisked Away, a company founded last year that specializes in surprise vacations, telling them the dates they wanted to leave, along with their budget. Two weeks before the Lawrences’ honeymoon, Whisked Away sent them an e-mail with what kind of weather they can expect, packing suggestions, and the time they should arrive at the airport.
“The only thing that made me nervous was not peeking at our packet before leaving for the airport, because what if I wished I had packed something else?” Kim Lawrence said. “It all worked out, though.”
The Charlotte, N.C., couple was sent to Copenhagen — a destination they wouldn’t have considered on their own, but one they loved nevertheless.
“The kindness of the people, the fact everyone spoke English, the biking culture, the food, being by the water — she really considered everything we loved about traveling and found a place that had all of it and more,” Jess Lawrence said.
Their only issue was the weather: It was warmer than predicted from the packet, so they took a half day to go shopping for lighter clothing.
Travel roulette has taken off recently, with a handful of companies offering everything from surprise trips and itineraries, to the simpler version where people plan their own roulette games and book the first thing they see, leaving the rest up to chance.
Since planning a trip takes so much research, by the time you actually get to the destination, you already feel like you’ve seen everything behind the computer screen, said Jose Toscano, cofounder and CEO of Jubel, a company that’s been planning surprise trips since 2015.
“This spoils the feeling of adventure, even if you go to exotic destinations,” Toscano said. “Real adventure requires an element of the unknown, that is what makes things exciting.”
Jubel has sent about 250 people on 120 surprise trips over the past two years, everywhere from Ecuador to Botswana.
Each traveler via Jubel receives a travel packet explaining practical info like the weather, along with the scenery (mountains versus urban), activities (boat trips, countryside tours, market visits, etc.), and a few blurbs about the destination. For example: “This destination often flies under the radar, and much of the time is left forgotten. However, it is a country with immense beauty and magical landscapes. Let yourself be transported into another fairytale-like world of misty lakes, towering mountains, lush forests and picturesque towns.”
It’s a very similar concept to Whisked Away, which encourages clients to livestream themselves opening their curated itinerary and surprise destination.
“It’s all part of the appeal,” said Charlotte McGhee, founder of Whisked Away. The other part of the appeal: not having to pour over travel reviews or ask social media where they should go.
“With surprise travel, they don’t have to decide or to spend any time planning,” McGhee said.
It’s not necessary to play travel roulette via a travel company, however.
Sean Pour, a backend developer at SellMax in San Diego, travels full time, and he gives himself a surprise holiday every time he books a flight.
He logs onto Wow Air’s website, and chooses the best flight deal — to anywhere as long as he hasn’t been there. So essentially, the deals select his destination. He chooses the deal the same day that he gets bored with his current destination.
Pour describes himself as a digital nomad, and he packs everything he owns: four shirts, two pairs of jeans, casual shoes, running shoes, and his laptop — into his suitcase and he leaves.
“It might sound strange, but some of the places I didn’t think I would like became my favorite,” Pour said.
Ho Chi Minh City in Vietnam was one of those destinations. He wasn’t too pleased that it was the lowest deal that day, but he’s happy he went. Same for Denmark, where he loved the culture, the cleanliness, and the food.
“The best part of it is that it ended up winning the award for the best place to visit in 2019 on Lonely Planet — but thanks to travel roulette, I was able to visit the place before it became mainstream,” Pour said.
Pour’s traveling method is a little extreme, but there are ways to play the game without going so overboard.
Brian Mano, 40, of Rockville, Md., used to travel to a beach annually with his three best friends . . . until they decided that they could go anywhere and have fun together.
So they began giving Mano’s mother — a travel agent — a pile of cash, telling her each year to choose the destination for them during spring break to anywhere semi-local (usually in the United States).
A week before the trip, his mother sends them each an envelope telling them the airline, and what time to get to the airport. They don’t know anything until they arrive at the ticket counter, punch in their information, and discover their destination. Even then, there may be an unexpected layover that could send them in a new direction.
“We find something unique and memorable in every destination,” Mano said.
The only issue with his semi-homemade style of travel roulette?
Mano’s mother doesn’t reveal the weather in their destination ahead of time.
One year, they went to Arizona, and the following year, they landed in Toronto.
“We were freezing in Toronto — we packed shorts,” Mano said. “Now, we pack a little of everything.”