#1 You are both in your fifties. You schedule the wedding at the end of March so that the kids can come on their spring breaks from college and grad school. Now they’re back at school and the two of you have a chance to take a vacation, your honeymoon week, without children for the first time in 28 years. Since you live in New York, you’ve been to the Caribbean plenty (with your former spouses), and Paris is so clichéd. And with college and the wedding, you don’t have a whole lot of money. Where do you go?
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#2 You and your foodie friends have eaten your way through Paris, Tuscany, and, after all that foam-obsessed fuss, Barcelona. Now what?
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#3 You’re graduating from Brown in June. You can’t bear the idea of job hunting in an ever-more outsourced economy, and your stepmother turned your bedroom into a yoga studio. You have three months, $4,200 in bar mitzvah money, and a jones for some serious soul searching.
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#4You wanna rock, but you’re so over the New York scene. You liked the Yeah Yeah Yeahs till their last album; now you call them the No No Nos. And you still can’t believe you aren’t allowed to smoke a damn cigarette at a club in this town.
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#5 Your phone is ringing, your e-mails are piling up, and your BlackBerry, set to vibrate, is buzzing and hopping around your desk like mad. You don’t just need a vacation. You need peace. Deep inner peace.
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#6 Disney World is out of the question. Your frighteningly brainy 10-year-old vetoed a trip there on the grounds that Mickey Mouse is the product of watered-down, commodified entertainment. Your already status-conscious 7-year-old, meanwhile, says no one cool goes to Europe anymore. Your citified children need some serious de-citifying.
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#7 You are a type-A thrill seeker. Your shrink says you may be bipolar, but never mind that. You know. You’re working on it. At the moment, though, you have some time off and want to go to somewhere dangerous—but you don’t actually want to get killed.
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#8 Your girlfriend says it’s over. Last night at Pastis, she told you that Paolo, that photographer she met at the Prada shoot last month, is “more than just a friend.”
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#9 Your boyfriend says it’s over. Last night at Balthazar, he (Paolo) told you the girl he met at the Prada shoot last month is …
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#10 Your $1.2 million bonus from Goldman Sachs has been cooling off in an index fund since January. Now it’s spring: The sun is shining, the birds are chirping, the supermodels are sundress-shopping, and you’d like to get as far away as possible from what you earned that bonus for. A little adventure might be nice. So would Wall Street luxury.
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#11 Your mother-in-law is coming, and she wants to stay at your place. She didn’t buy your lack-of-space or potentially- lethal-mold arguments. You need a weekend escape plan.
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#12 Your wife is turning 40. In thirteen years of marriage, she has graced your life with more brains, beauty, and charm than you rightfully deserve, endured your alternating bouts of professional self-aggrandizement and crushing self-loathing, and birthed your children—10-year-old Duncan and 7-year-old Olivia and Brooke (the twins). You owe her. Big.
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13 You remember how you felt about tourists coming to New York after 9/11. Even though you thought it might somehow feel wrong, it somehow felt right.Now you’d like to go to Madrid.
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14 You and your wife both retired last year. Now you’ve got nothing but time. You’ve always wanted to go to India, but you’ve never been farther than Curry Hill. Bombay and Delhi are too obvious. You want something more exotic.
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15 You are an architecture and design geek. You’ve been to Bilbao; you’ve seen the Villa Savoye. Now you keep hearing about Houston. Houston?
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16 You’re planning a family reunion. Your brother the narcissistic surgeon was too busy. Your sister the installation artist was “in a bad head space.” Which left it to you to come up with something—when it was their stupid idea to begin with.
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17 You are a rising corporate star. Headhunters have been calling for a year with offers, but this time, you bit: double your salary, an office overlooking the Hudson, equity partnership. You negotiated a week off between jobs, and you’d definitely like to celebrate. But if you were the type to lie on a beach, you wouldn’t have landed this gig in the first place.
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18 You’re single—and looking. But you don’t want to go on some sleazy pickup trip.
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19Microsoft wants to buy your software start-up, but only if you come with. You’re ready to cash in, but are you ready to abandon Manhattan for Seattle? It’s Thursday—Microsoft needs a yes or no by Monday. You have three days to decide.
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20 Your daughter is 2. Until now, you’ve been maintaining the illusion that a vacation is a time to sleep in, sip espresso in a Belleville café, and have sex on 400-thread-count sheets in the middle of the afternoon. But after last year’s “vacation”—no nanny, no sleep, certainly no sex—you realize that it’s time to give in to the all-inclusive package deal, child care included.
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21 Last year on St. Barts, you stayed in a $600-a-night hotel a coconut’s throw from people living in tin-roof shacks. The cognitive dissonance made your head hurt. This year, you’d like your island sun and fun without the fuss—or bourgeois guilt.
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22 Soho is so eighties. Chelsea is so nineties. Long Island City is so aughts. But you want to see some art, maybe even buy a little something, and you don’t have the time or money to fly to Florence.
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23 You’re having an affair. You can convince your husband it’s a business trip, but you’d better be damn sure that you and your other significant other don’t run into anyone you know.
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24 You’re sending the kids to summer camp in the Adirondacks. Remember summer camp? Color war, capture the flag, the girls across the lake … But wait, if you’re dropping off the kids, that means you and your wife are on your own. In the Adirondacks!
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25 You’re having wardrobe issues. Serious wardrobe issues. Midlife-crisis-size wardrobe issues. For the first time, you’re even contemplating that most decadent of retail adventures: the Paris weekend shopping spree.
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