The Magical Mystery Trip

Every year, seven friends make it a priority to get away from kids, spouses, and responsibilites and have a little fun.

  • Sarah Humphreys
We call our annual surprise vacation the Great Escape. The title has nothing to do with the World War II movie (so don’t read into it too much). It’s just the perfect name for the perfect friends’ getaway: a fantastic sabbatical from our very busy lives. The seven of us first met while at Williams College, in Williamstown, Massachusetts. Now we’re all in our mid-30s and working variously as a lobbyist, a veterinarian, a landscape architect, a stay-at-home mom, a marketing director, a conflict-resolution consultant, and the executive editor of Real Simple (that’s me). We’re scattered all along the East Coast; single, engaged, or married; and have anywhere from zero to three kids. What we have in common: We’re all pretty much type-A personalities who spend most of our lives being in charge, dependable, and responsible―and therefore desperately in need of a break.

The idea for the trip originally came from Gigi, back in 2000 or so, when we were just a couple of years out of college. She knew a group of guys who did it―each took a turn organizing a mystery vacation for the rest of the group to someplace exotic: India, Bali, the Bahamas. And though we weren’t exactly the take-off-to-India types (due to a shortage of money, not to mention time), we loved the concept. We also loved the fact that this annual trip guaranteed we would always have a chance to see one another―something that becomes more difficult with each passing year, no matter who your friends are or where you know them from.

Here’s how the Great Escape works: Each year, one person in the group is designated the Planner; that responsibility rotates until everyone has had a turn (and then we’ll start all over again). The entire group settles on a per-person budget and a long, four-day weekend that works for us all. Then the Planner is left to decide and arrange the rest―where we go, where we stay, what we do, what we eat―and be very resourceful about all of it, since the budget has to cover absolutely everything, from airfare to afternoon snacks. As for the six Nonplanners? They remain in the dark until a few days before the trip. That’s when the secret location is revealed via a series of clues and they’re given marching orders. Think of it this way: After one year of playing cruise director, we are rewarded with six years of playing lounge lizard, sitting up only to dip another chip.

We’ve always been a close-knit group. Over the years, we’ve hopped on planes to help one another cope with a breakup, update a clothes closet, or even spring-clean a home. (We once removed two tons of junk from Debbie’s apartment―kid not.) But the Great Escape is different. "It feels really self-indulgent, and I love that," says Carrie. "We can truly check out and be with the friends who know us best." "This is the one time all year when I escape life with kids," adds Chandler, who has three. "It’s a totally different pace." And this from Gigi: "We know how important the trip is to each other―it’s sacred. And so unless you’re really incapacitated, you’re going." Over the years, friends have had to skip the trip because they were too pregnant or arrive a day late because of family obligations. But we do make a herculean effort to be there, even if it means coming straight from a honeymoon (Debbie) or delaying the start of a big, new job (me). 
 
Our first Great Escape took place in 2004. Mary was deemed the inaugural Planner, and she rented a great house for us in Stowe, Vermont. It rained for four days straight, but we couldn’t have been happier. It was just us―no husbands or boyfriends, no friends of friends, no kids or makeup. We could be sentimental and snarky, uncensored and unapologetic. We could vote on who had the prettiest hands and the ugliest feet (Debbie on both counts). We were hooked.

The picture here is from Great Escape 2008, which happened last August. Debbie was the Planner, and she took us to Cordillera, Colorado, just outside Vail, where we stayed (for free!) in a fabulous house owned by her sister-in-law’s family. "It was so fun to watch this trip come to fruition―and see my friends enjoying everything I had in store for them," says Debbie. Since we had a photographer in tow on the trip, we were admittedly a little more active than usual―hiking, horseback riding, and feeding a domesticated buffalo. But most years the daily itinerary goes something like this: We wake up when we wake up. Breakfast is eggs and bacon. We maybe shower. We maybe dress. We eat lunch and Gigi’s mint brownies. We try to do some sort of outdoor activity. By then it’s time for a couple of rounds of Clue and Dark and Stormies. And then we go out to a great dinner, then go to bed.

"There’s something about the ritualistic nature of the trip that’s comforting," says Gigi. "No matter where we go, I know I’m going to spend the weekend doing the same sorts of things with the same close friends, who are, deep down, the same people no matter what seems to be going on. In an unpredictable world, it’s a predictable thing."

The unpredictable world makes for good chats, though. We all come to the Great Escape with banked issues to discuss. We solve stuff. It was during one of these serious life discussions a couple of years ago that I so wisely said, "Life gets harder, but it gets richer." I’m still regretting that.

But, no, we’re not always that deep. As much as we need the group therapy, we need the comic relief, too. A lot of time is spent cracking jokes that are surely not funny to anyone else but us, playing with a Ouija board (which has yet to make an accurate prediction), and impersonating reality-show Bachelorettes and Real Housewives. "Time flies, and we laugh until our cheeks hurt," says Mary. We get to be the best―and worst―versions of ourselves (in a good way).

We’re now six years into our Great Escape tradition―one marriage, seven children, nine moves, and 11 job changes further along than we were that first year. Life just keeps getting harder but, ahem, richer. And yet we’re already wondering where Chandler is planning to take us for Great Escape 2010. And we’re dreaming big for Great Escapes 2011 and beyond. We’ll up the budget, extend the dates, wave good-bye to our families, and head to more exotic locations, such as Tuscany and Costa Rica and Kenya. And there we’ll curl up on cushy couches, like blissful limp noodles, and just be our sentimental, snarky, uncensored, unapologetic selves.