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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.

By Sarah Humphreys
Desert scenery with women on horseback Ken Kochey
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). 
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