Do you miss your friends? The ones you never see? The ones you met in college, or camp, or nursery school, and still cherish beyond measure even though adult life precludes you from getting together pretty much ever? It may be time for a Mystery Trip.

By Sarah Collins
Updated July 27, 2015
Women running to the end of pier
Credit: altrendo images/Getty Images

In a nutshell, a Mystery Trip is when a group of friends decides on a date and a budget and one member of the group takes charge of all the planning (from flights to lodging to meals), only revealing the destination to the rest of the friends right before they leave. You rotate who plans it every year.

I’m the executive editor of Real Simple; I’ve been doing this trip with my 6 college friends every year since 2004 (and I wrote about the experience for RS back in 2010). Last week, a woman named Jen Kattner emailed me from Texas and told me all about her own Mystery Trip, which she started with her 6 childhood friends after reading the article. Five years later, they’re still going strong. As Jen wrote in her email, “The trip is essential to our friendship. The older we get, the busier. The more kids, the less often we see one another. The bigger the job, the more it demands. But we know there will always be one week we can get back to our roots, share a bottle of wine, lots of laughs, and most always happy tears, too.” Cool, huh?

I figured it was time to write a step-by-step guide (with a little help from Jen) for pulling this trip off, in case others may want to make it an annual tradition (highly recommended).

  1. Plan waaaaay in advance: I’m talking a year out or more. Get the trip on the calendar and carve it in stone so it trumps the million other obligations that will definitely crop up. For the trip to succeed, it has to be sacred: The only times my friends and I have missed it are for late-stage pregnancies or just-born babies.
  2. Don’t invite others. Just being honest here. Opening it up to people beyond the Founding Friends changes the group dynamic, complicates scheduling, and encourages more requests from outsiders in the future (which you’ll either have to agree to or turn down—and feel guilty). Exception to the rule: This year Jen’s group allowed members to “bring a sister, which only resulted in one sister but she might as well have been all of ours since we’ve known her since birth,” says Jen.
  3. Five days is ideal: Any longer and it makes it hard for friends to commit; any shorter and it’s too short! (Plus it limits how far you can go.) My friends usually do a Wednesday-Sunday sort of thing. Some join on Thursday, depending on the madness level at home.
  4. Relax about the budget. We started with a $400/person budget and have worked our way up to $1500/person. But you can plan a fantastic trip on a shoestring, seriously. Jen agrees: “The destination is always a bonus but the real fun comes in the togetherness. We often joke about how we could hole up in one of our homes for a few days and have just as much fun.” To keep it cheap, go somewhere within driving distance for most. Mooch off others for lodging (one year when I was the planner, I kicked my parents out of their RI house so we could stay there). Cook at home.
  5. Have fun with the big reveal. In my group of friends, the planner starts to email riddles about a week before the trip and we all drive ourselves crazy guessing where we’re going. Jen’s group does it even better. The planner will send funny clues (sand, underwear) in the mail and give hints about what to pack. But everyone’s left in the dark till the day of. “We usually meet at someone’s house nearest to the airport the night before and spend all night contemplating where we are heading the next day. The reveal always includes luggage tags. We get to the airport and give them out and make a video of our reactions.”
  6. Be as organized (or loose) as you want. In planning the trip and tracking the budget, some of my friends produce meticulously itemized spreadsheets and itineraries, down to the garnish on our drinks; others tend to wing it more. Let your personality drive how you plan, and don’t feel pressure to be perfect. Remember: All the others really care about is that you’re all together and they didn’t have to lift a finger to get there.
  7. Make comfy couches a prerequisite... Based on my group’s experience, there is a lot of time spent sitting and talking. Big, comfortable couches help facilitate this. When a planner researches rental houses, comfy couches are among the top search criteria.
  8. …But do plan a few activities. Don’t let the couches suck you in completely—get out and enjoy your destination. Some of our best Mystery Trip memories come from the stuff we’ve done: riding horses at a dude ranch in Colorado, kayaking in a bioluminescent bay in Puerto Rico, visiting the Ben & Jerry’s factory in Vermont.
  9. Honor mini traditions. These will come naturally, and they add even more deliciousness to the trip. No matter where we go, the planner brings a pan of brownies topped with mint frosting for us to devour, we drink Dark & Stormy cocktails, and we play Clue. There’s no rhyme or reason to any of this, but we did all of these things on our inaugural trip to Stowe, VT, in 2004, and they’ve become part of the package.
  10. Don’t forget the souvenirs! I drink out of my Mystery Trip coffee mug (from 2012, the year we went to Kennebunkport, ME) every morning.