The Road to Ruin: 10 Ways to Wreck Your Holiday

What’s worse than a soggy vacation? Raining on your own parade. It can happen through hazy planning, a stormy disposition, or cloudy logic. But here’s a brighter forecast: Overcome these self-inflicted vacation tempests and your next getaway will be sunny days and smooth sailing.

Bad Habit #1: Packing a bad attitude

Travel can be hard—a reality that cheery articles elide. From the mundane (jetlag, language barriers, faulty directions) to the truly trying (lost luggage, food sickness, price gouging) hitting the road can be a punch to the gut. But remember this: Authentic travel means placing yourself in new contexts and challenging your assumptions. If you travel patiently you protect yourself from being overwhelmed by transition shock—the number-one attitude killer and fuel for the avalanche effect of negativity. So take time to adapt to a world unlike your own and don’t give in to cynical judgments or broad generalizations. Remember your own needs—napping, refueling, reading, or whatever it takes for you to transition with positivity.

Quick fix: Cultivate “an attitude of gratitude.” You’ll be amazed at how quickly the world acknowledges your expression of openness.

Bad Habit #2: Wearing a grumpy face

A gloomy disposition is internal; a sour expression is out there for everyone to see. Your dyspeptic look tells the world that you’re anxious, skeptical, mistrustful, out of place, and aware of your own foreignness. In short, you don’t look like yourself. So turn the beat around: Imagine that you’re on the vacation you’ve dreamed about. Imagine that the locals are friendly and engaging. Imagine that you could have a successful and enlightening conversation. Present a face that says, “I’m happy to be here now.” And about your fears that a smile will make you an easy target for pickpockets and Parisians: Relax—the pickpockets already have your number and the Parisians will ask for your number when they see the real you.

Quick fix: Turn that frown upside down. Practice smiling in the mirror and challenge yourself to adopt a cheerful expression. No one thinks you’re a local anyway—but they won’t be able to deny your kindly comportment.

Bad Habit #3: Being cheap

What’s the most expensive element of travel? It’s not airfare, hotels, or luxury shopping. It’s time. Time is your most valuable commodity and your chief investment in a holiday. Don’t limit the promise of your getaway by becoming a tightwad on the road. You won’t make up for a $2,000 air ticket by nickel and diming the rest of your vacation. In fact, miserliness can damage your trip by injecting bad attitudes, wasted time, and arguments into the equation. None of this means you should spend wantonly. Instead, you should plan better by lingering longer in fewer places, dining out at local favorites (not Michelin stars), and avoiding shopping splurges.

Quick fix: Don’t be penny-wise and pound-foolish. Will a cab save you two hours? Take it. Will a flight save you a day? Book it. Think you can decode Angkor Wat on your own? You can’t—hire a guide. And don’t bargain to death. What you’ll remember will be travel enlightenment in the absence of pecuniary piddling.

Bad Habit #4: Doing absolutely everything

Rome wasn’t built in a day—and it can’t be seen in a day either. So you have two options: Either plan a few days in Rome and plot an achievable itinerary that creates time for your must-see sights or, if you only have a day in Rome, choose three things to do and promise to return for the rest another time. Don’t overplan and run yourself ragged by packing an entire city and its civilizations into a madcap maze of manic touring. Not only would that be psychologically and physically masochistic, but it also assumes that you’re actually able to remember what you did and what you learned. Worst of all, travel panic leaves no time for serendipity—for the sorts of delightful and defining moments that make traveling memorable and rewarding.

Quick fix: Slow and steady wins the race, so pace yourself. Check your great expectations at the door and create space in your itinerary for surprise discoveries, spontaneous ideas, and relaxing moments.

Bad Habit #5: Obsessing over your iPhone

Once upon a time, before there was such a thing as a local data plan, there were maps, guidebooks, notes, and even human beings who could interact and share information. These resources still exist but, like birdsong smothered by a jackhammer, they’re harder and harder to perceive. The problem with compulsive app-ing is that it chips away at the very thing that makes travel rewarding: a sense of engagement and discovery. Since it’s difficult to discover something when Google knows everything, a smartphone can at times wreck the qualities of communication, intuition, and experimentation that travel rewards. Not that technology should be left at home, but it should be considered a controlled substance on the road—a problem-solving tool but not a constant companion.

Quick fix: Unplug. Put down the phone and embark on a digital vacation. Use the rest of your life for texting, tweeting, and checking work emails.

Bad Habit #6: Shopping at your favorite store

Ever wonder what the Gap looks like in Tokyo or what Jo Malone sells in Cape Town? You shouldn’t—it’s the same thing. They’re called chain stores for a reason: They offer similar products all around the world. So why are you spending valuable time on your vacation verifying the supply-chain management practices of big box retailers? Skip the usual suspects in the luxury mall. Sashay past Zara. Don’t even think about Starbucks or H&M. When you’ve made the effort to travel to a faraway place, what good do you achieve by searching for superficial similarities when you should be embracing cultural distinctions?

Quick fix: Go local. A more revealing (and less expensive) way to get in touch with a place is by gravitating to local grocery stores and markets. You’ll discover what people eat, how much they pay for it, what they talk about when they shop, and more. If you have a passion for fashion, visit small retailers or, better yet, go to fabric stores and tailors and have clothes custom-made.

Bad Habit #7: Yammering about yourself

Guess what winemakers don’t want to hear about? All the other wineries you’ve visited in your life. Travel is a chance to leave yourself behind. The quality that turns people on is curiosity, because it suggests genuine interest and a willingness to listen. When you visit a new place you have more to gain through active listening than by incessant talking. So play the role of travel detective and start asking questions. You’ll be surprised at how forthcoming a stranger can become once you express personal interest in their life and homeland.

Quick fix: Input not output. Switch your brain from “send” to “receive” mode. Open all your senses to the new world around you, ask genuine questions, and give your judgments and insecurities a much needed vacation as well.

Bad Habit #8: Going gonzo!

What do snake wine shots, sloppy tattoos, and Bo Derek braids have in common? The Y.O.L.O.* mantra, which promises to turn every traveler into Keith Richards. Do you remember when he cracked open his head climbing a coconut tree while on holiday in Fiji? Right. The road is an ideal place to experiment and push your boundaries, but the good judgment that turned you into a traveler is also your most reliable guide. Gobbling up all the bizarre food you can find will make you sick sooner than it will make you Andrew Zimmern (who is a surprisingly intentional eater). Jetting off to an uncharted place won’t turn you into Anderson Cooper—but could land you in a heap of trouble. And becoming a midnight bacchanalian is a lot more Lindsay Lohan than Lou Reed. Travel is a chance to remember who you are beneath the restrictions and responsibilities of everyday life and to discover who you can be in a new context. But good judgment, a sense of your own limitations, and perhaps a late-night cost-benefit analysis are among your wisest travel companions. (*You only live once)

Quick fix: Let conscience, not carpe diem, be your guide. Ben Franklin said it best: “Moderation in all things—including moderation.”

Bad Habit #9: Taking only my advice

Journalists never rely on only one source, and neither should you. Even the best intentioned trip advisor has inconsistencies, biases, and memory failures that reinforce the subjectivity of their travel experiences. The solution is to use multiple sources to cross-check your travel ideas for price, value, reputation, location, deliciousness, vibe, color scheme, flavor, noise level, hipness, tranquility, or whatever other quality is most important to you. Here’s an added benefit of being a crafty researcher: Through triangulation you’ll start to engage with your destination, learn its landmarks and contours, meet its denizens, and discover its delights as confirmed by many sources.

Quick fix: Look before you leap. Don’t tackle your research in a day; instead, make travel planning fun by Googling in short spurts over time. Ask traveling pals and Facebook friends for insights, hidden gems, or new discoveries. And visit multiple websites before making bookings.

Bad Habit #10: Making everyone else happy

Were you the “peacemaker” as a child? Were you the congenial kid, gracefully navigating around conflict, sacrificing your own joy for the greater good? How’s that working out for you? The tough love truth is that your holiday happiness is your own responsibility. And your challenge is to take an active role in defining your vacation aspirations and devising a plan for achieving them. It’s not easy—your travel companions will certainly have wish lists of their own. But don’t be the kind-hearted sucker who spends the day antiquing in Ubud when you wanted to see the seaside temple at Uluwatu. It’s nobody’s fault but yours when you fail to communicate to others your must-sees and must-dos.

Quick fix: Lean in. Own your vacation and articulate your holiday hopes. You may be surprised by how quickly your companions embrace your ideas and join you. If no one is on board for your essential activity, do it on your own. It may cost a bit more to go solo, but aren’t your dreams worth it?