The Type-A Guide to Vacation Planning

We know, we know: there’s a sense of security that comes from having your vacation planned down to the last minute. But it’s also a sure-fire way to miss out on all the spontaneous adventures that might come up during your trip. Case in point: I once passed on the opportunity to go sailing with a bunch of cool strangers I met on the beach to see otters at The Florida Aquarium. Hindsight 20/20 …

If you’re going to freak out over something, let it be your airfare. Because if there’s one thing that can ruin a vacation, it’s a bad flight. So, nitpick over the fares, the baggage fees, the seat selection, the connecting flights, the location of the airport relative to your hotel, and all other flying-related considerations. And if you’re trying to decide between a pricey direct flight or a cheap one with tight connections, go for the former every time, because trust me—you can’t put a price on getting there with your sanity in check.

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If you’ve been asked to set up dinner reservations for a large group, know that you’ve been set up to fail. Because, here’s the thing: you’re not going to find a place that can accommodate your oversized party AND cater to your friend's food allergy, your cousin's aversion to seafood, your sister's reluctance to pay more than $15 for an entrée, and your dad's refusal to pay an 18% gratuity. See? A no-win. So, hold the phone on making those dinner resos, and adopt a self-serve approach to vacation dining.

Accommodations is another area where we’ll give you free rein for letting your crazy out. Why? Because if you pick a bad hotel—say, one with a crappy location or questionable hygiene standards—it’ll undoubtedly cast a shadow over the rest of your vacation. Basic requirements to look for in your search: adequate security, convenient check-in/check-out times, solid service, a central location, and ample amenities.

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Remember in high school when you ended up doing 90% of every group assignment? Yeah, well, jump into go-getter mode the minute you step off the plane and we guarantee you’ll be forever responsible for organizing activities, tours, hula dancing lessons, you name it. The moral of the story? Just say no.

There’s always one person in the group who wants to make it rain, cash-wise, on vacation. She’s making dinner reservations at Michelin-starred restaurants, pleading with you to splurge on a suite, and sulking when you won’t drop thousands to sit in first-class. Our advice? Resist caving, and stick to your penny-pinching guns. Your bank account will thank you later.

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It’s true: torrential downpour is most definitely going to compromise your plans for Hawaiian beach vacay. But we can also say with certainty that moping around indoors and obsessively checking the forecast will only make matters worse. Instead, try adopting a sunny outlook (ha — get it), then look into other ways (shopping, spa-ing) to spend your day. I promise the sun will be out before you know it.

You could plan the vacation of the century. There could be five-star accommodations, first-class airfare, and a personal meet-and-greet with Beyoncé. And trust me, some people will still find a reason to moan and groan and compare it to the trip they took to Aruba ten years ago. The takeaway: don’t waste your energy worrying about whether other people are having fun. You are responsible for you and your happiness alone.