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The Key to Avoiding a Vacation From Hell? Don't Book One There

Every vacation destination has its own personality; and if that personality sucks, then chances are your vacation is going to suck, too. That's just math.
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So, you want to go on vacation. You've already figured out who's going, but you still haven't decided where. In case you're thinking, "It doesn't really matter where we go, as long as I'm with people I love," keep reading because I'm about to totally save your vacation.

The thing is, I used to think like you. Then I learned a really hard lesson -- one that was so grueling and miserable that I vowed to do whatever I could to save other people from having to go through the same thing.

Here's what happened to me: My besties and I went camping. In an actual tent. At the beach. And it was the third-worst experience I've had in my entire life, right behind going through a divorce and my dad passing away. I bailed after one night and drove all the way back to Austin. When I walked through my front door, I literally fell to my knees and kissed the floor of my entryway. I'm not even making that up.

That experience taught me that no matter how awesome and cool my friends are (and they are), when it comes to vacations, where you go matters every bit as much as who you go with. And there's a simple reason for this: Every vacation destination has its own personality; and if that personality sucks, then chances are your vacation is going to suck, too. That's just math.

And even if your vacation destination's personality doesn't full-on suck, but simply grates on your nerves, that can still dramatically increase the chances for a less-than-fun vacation. Because it's not simply that the annoying personality is along for the ride, she's actually hosting you. You're staying at her uncomfortable house. You're hanging out in all of her no-fun favorite places. You're running into all of her insufferable friends. There's no getting away from her!

The key to avoiding this type of vacation disaster is being aware of the different personalities of various vacation destinations, and making an informed choice -- one that will be a good fit for you and your traveling companions. In order to give you a head start, I've created a list that gives you the lowdown on the personalities of a handful of popular destinations.

New Orleans: New Orleans is like your colorful friend from an established-yet-eccentric family. She's super outgoing and uninhibited, loves all kinds of food, and is game for just about anything. In short, she can be a total blast. But as is often the case with people who can outdrink everybody, she has a tendency to take things too far. More often than not, a night out with her involves you holding her hair back while she throws up on the curb. Note I said "involves" not "ends with," because as far as she's concerned, throwing up just makes room for more alcohol. Another downside? She's not above peeing in alleys.

Taos: Dude, Taos is, like, totally laid back. But not in a Dazed and Confused kind of way. He's more like Dazed and Enlightened, brah. His love for nature runs as deep as the Rio Grande Gorge. And all of that amore for the outdoors can really stoke an appetite, if you know what I'm saying. Luckily, there are plenty of great restaurants to choose from. The downside of this super chill cat is that after a while you wish he'd stop talking about GMOs long enough to get a J.O.B. After all, he has his Ph. F'ing D. (Granted, it's in organic botany; but still, if there was ever a place where an organic botanist could find a job, it'd be here.) In other words, you can hang out with Taos for a long weekend, but any longer than that and you can get really sick of his sh*t.

Santa Fe: Oh, Santa Fe. She's so crystalicious, you just want to group hug every last smudge stick of karma right out of her. In her past life, she was a stay-at-home mom in Dallas. But after the kids were grown and she got that divorce, she went on a retreat to "find" herself. A couple of hours into the teepee sweat bath she had a vision of herself as an integral part of the natural fiber tapestry that is the arts scene here. So, she took her half of the proceeds from the sale of the McMansion and bought a gallery on Canyon Road, and the rest is "herstory." Santa Fe has a taste for the finer things, but her overemphasis on being deeply-spiritual-while-not-conventionally-religious and her love for all things Native American get pretty tiresome after a while.

Beverly Hills: Remember Amber (played by Kate Upton) in the movie The Other Woman? Amber was not at all smart, but she was really pretty and genuinely nice. That's Beverly Hills. She is aware of her strengths and weaknesses, and doesn't try to pretend to be something she's not. Her only objectives are to be friendly to everyone, and to be as perfect as possible. If you're looking for intellectual stimulation, you've come to the wrong place. But if you want a location where the air outside smells like the waiting area of the spa at the W Hotel, and you're game for a delightful conversation over a delicious cocktail by a sparkling pool in perfect weather, then you've come to the right place.

New York City: You can come visit NYC if you want, but don't expect him to lift a finger to make you feel at home. In addition to paying your own way, he considers it your obligation to pay his way, too. After all, he's allowing you to be in his presence, and anybody who knows anything agrees that he's the greatest. If you don't care for his personality or otherwise "get" him, that's not his problem. The truth is, he can take you or leave you. Occasionally, he's in a good mood; but his baseline is brooding, cold, and elusive. Smiling and making eye contact are not his style, and every item of clothing he owns is black. If you want to fit in while you're here, you should take your cues from him. But if you want go around looking like some modern day Minnie Pearl by wearing colorful clothing and saying "Howdy" to everyone you meet, go right ahead and embarrass yourself.

Las Vegas: Las Vegas is like a twenty-one year old girl from a family that recently struck it rich when sales of their homemade energy drink went through the roof. They used to make special orders of it in small batches in ice chests in their garage, but when a popular pro-wrestler declared it his secret weapon, the family business pumped all the way up to mega corporation-size. Their first splurge was Camaros for all the kids. After that, they became obsessed with tearing down, rebuilding, remodeling, and adding onto their house. They even have an Eiffel Tower in their backyard. What they lack in class and taste, they make up for in size, volume, sparkles, and cleavage. They can they be really entertaining in a "reality" show kind of way; but when you roll with them, you run the risk of going on a spending bender, and waking up broke.

If your destination is not on my list, don't worry. This is something you can figure out for yourself. Simply Google around for articles on the places you are considering. Then based on what you find out, simply imagine each destination as a person. Is that the kind of person you want to spend your precious few days off from work hanging out with? If so, enjoy! If not, keep researching.