Travel Company Plans Mystery Trips

One of Denise Chaykun’s close friends had been stressed out for months. One day, while she was listening to him talk about how busy he was with work and what a toll that was taking on him, she was struck by an idea.

“My solution to everything is you need a vacation,” Chaykun tells BTR. “So that’s what I told him. He said he didn’t have time to plan one, so I said I’d do it for him.”

Chaykun had always enjoyed travel planning and figured doing it for one of her friends would be fun. As she started the process, she joked with her friend about how cool it would be if she knew where he was going and he didn’t, like a mystery trip.

“I said give me your budget, give me your credit card, do you trust me,” she laughs. “He leapt at the idea.”

So Chaykun created a mystery vacation for her friend, noticing that as his travel dates approached his anticipation built and he shared his excitement with all his friends and family. When the trip went off without a hitch (he ended up in San Francisco) Chaykun realized “something was there,” and set about researching what it would take to build a company around the concept of surprise.

Thus was born Magical Mystery Tours. In the five years since its inception, the company has been featured across Men’s Journal, Travel Weekly, SmarterTravel,, O the Oprah Magazine, and so many more.

BTR sat down with Chaykun to talk about mystery travel and how she and her husband ended up in the French Riviera a few weeks ago.

BreakThruRadio (BTR): Okay, so how does this work?

Denise Chaykun (DC): It’s a very controlled process and I think a lot of people hear mystery trip and think it’s crazy exotic and we’re going to send you somewhere you might not like. We definitely have travelers who like crazy–we had one girl that said “I don’t care, send me to a yak farm in Mongolia and I’ll love it!” But we have a questionnaire on our website that’s pretty extensive, which goes over basic things like what we need to know for your tickets, but also, where have you been and what do you want out of this vacation.

You set your budget, how long you’re going for, and let us know if you are a Ritz-Carlton person or cool with someplace clean and your own room and bathroom. Apart from that, you can give us as many parameters as you want.

BTR: When does the traveler give the final okay?

DC: After that, you put down an initial deposit, we do our preliminary research and say, “Ok, we have something lined up for you for these dates for this price. You go ahead and pay us and we’ll book it.” Then a week out you get a weather report and a packing list, and then a packet in the mail a few days ahead of time with a sticker on it that says open at airport. That packet will tell you everything you need to know!

BTR: Is there a minimum or maximum amount of days you can go for?

DC: There is a huge range; we have done everything from a weekend trip, which naturally means you’re probably not going halfway across the world, to a trip that was close to three weeks, and with more time and a bigger budget you can get into some serious adventure.

BTR: Can families do it?

DC: We’ve had everything! We’ve definitely have a ton of couples; we’ve had families and multigenerational travelers; we’ve had friends who are all spread out across the country and need to get together and can’t decide where, but also definitely individual travelers as well.

BTR: What are some of your favorite mystery vacations you guys have planned?

DC: I think the vacations that are really amazing are the “trip of a lifetime” ones, like a 25th anniversary where these people have been saving forever for this and have never been out of the country, or we just had a couple where one of them had just gotten over cancer and this was their celebration… The high school graduation trips, or anything that is super special for the people going and pushes their boundaries and does something new for them.

I think the magic part of the mystery is that they get to focus on the experience and just enjoy it, instead of spending months ahead of time planning it and feeling like they have to, you know, research every restaurant in a city and pick the perfect one. Instead, they know that all that is taken care of.

BTR: It probably also helps people enjoy their trip more when they focus on what they want to get out of it, rather than where they are going.

DC: Totally, I have a personal example that really illustrates that. I just went on my honeymoon last month and it was the perfect opportunity for a mystery trip. Given all my involvement with travel, I will totally over-plan a trip. Going into it I knew that if I was planning it I would have us in five countries in two weeks, a different hotel every night, seeing everything and going everywhere. But deep down I knew that wouldn’t really be fun, it’s just I can’t help it. So in the process of booking the mystery tour I was like, “We need to relax.” We want to see new things and experience new things, but this isn’t a Paris, Tokyo, and London all-in-one trip kind of thing.

We ended up in the French Riviera and it was amazing, not somewhere I would have thought of, but it was perfect and different. The experience was amazing. So it [also] keeps you from sabotaging your own travel plans.

For more on mystery travel tune into this week’s Twenty-Something Traveler!

Feature photo courtesy of Giuseppe Milo.