Eight Mistakes You’re Probably Making When You Travel – Travel Hacks



Photo by Jaysin Trevino

If you’ve traveled at all in the last decade, you’ve probably encountered travel stress. It’s counter-intuitive: we take vacations, honeymoons, and family trips in order to escape the rigors of everyday life, not to compound them. Yet, if we’re being completely honest, even our best vacations probably included some moments of sheer frustration. Sure, some hassle is to-be-expected. After all, we’re leaving our familiar routines and going to unfamiliar places, and that involves risk. But what if I told you that a great many of the things that interfere with our enjoyment could be engineered out of the experience?

A great deal of what people are doing when they travel is not working for them. Why else would tempers run so hot, couples get into arguments, and stress be so prevalent. A few years ago I set out to “hack” travel – to identify all the sources of stress I could, and experiment with engineering the stress out of the situation. Now that I sometimes wear the “travel blogger” hat, I’ve had fun trying out some of the latest innovations in travel, and I’ve accumulated a “laundry list” of the most common mistakes I’ve made – and seen – that have caused unnecessary stress. I’ll link from this article to more detailed pieces I’ve written and others have written, where necessary. This is by no means an omnibus list – it’s more like an “all star” catalog of the “hacks” you’re least likely to read anywhere else.

So, let’s get to it. Here, in descending order of most-fundamental to “nice-to-avoid”, are the eight travel mistakes you may not even know you’re making.

1. Trying to find the cheapest flight instead of the best value.

For me, there is no greater cause of travel stress than cancelled flights, bad service, and otherwise being marginalized by your airline. Unless you’re flying business or first class, the service of mainline carriers in the US can be abysmal. And when we book our own travel, we presumably travel for pleasure. Yet most of us still book a flight by going to Travelocity, Expedia, Orbitz, Priceline, or the flavor-of-the-week budget travel site, entering in our dates (some of are “hip” and use “flexible dates, as if those help), and choosing the cheapest possible flight (or cheapest all-jet flight, or cheapest non-red-eye flight). The end result is the same – you’re in steerage on one of the mainline domestic carriers, with a postage-stamp-sized bag of peanuts to tide you over if you’re lucky.

What varsity travelers know is this is rarely necessary. Without upgrading a class, the US has superior carriers. They’re called Virgin America and JetBlue. (I have no business affiliation with either.) I don’t evenĀ needĀ to get into the weeds of how the mainline carriers make most of their money on first and business class passengers and how, almost by definition, the “only coach” business model forces a carrier to value all its customers more, because these two outperform the legacy carriers in almost every survey.

On a vacation costing more than $1000, you could eliminate 98% of airline-related stress for only an extra $100-a-ticket, would you? What if I told you you didn’t even have to do that? Click here, then here, to read in greater detail about Kayak, the real flexible dates hack, and choosing real value in air travel.

Photo by S Diddy

2. Using an airport-based car rental service when you don’t need to.

I understand the reasoning, because I used to think the same way. You want your ground transportation to be a no brainer, so you book through Hertz, Budget, Enterprise, or one of their ilk. I’ve written a longer article about the hidden ways they may be costing you time and money, but suffice-it-to-say the experience can be anything but stress-free. Commute times from baggage-claim to the rental building and waiting in line at the rental counter, let alone issues with your reservation, can quickly cannibalize any time savings. I recommend seeing if there’s a Zipcar location nearby your hotel or nearby the airport. Before I get into why off-airport rental is no longer as inconvenient as it once was, let’s summarize the ways in which Zipcar(with whom I have no affiliation) is better than the airport-based agencies.

-Gas and insurance included.

-Better cars, often for still less money.

-All your information is saved, and there’s no need to wait in line – book from your smart phone, using a map to find the right location for you, and go right to the car when you arrive.

-More nimbly run, more effective company with infinitely better customer service.

Ok – so how do you make it happen? Many airports, like JFK, Seattle’s SEATAC, and San Francisco’s SFO have train lines connecting the airport directly to the city. What if, like New York’s LaGuardia, Chicago’s O’Hare, or LAX, they don’t? Glad you asked. Please read on to the next suggestion…

3. Not knowing about Uber.

What if somebody did for car services what Zipcar did for car rental? What if you could have all your billing data and preferences stored in an account, and summon a car via a GPS-based smartphone app? Enter Uber. For slightly more than the price of a yellow cab (or literally the price of a yellow cab, if any are “on the grid” in your area), you can now summon a personal car-and-driver to your exact GPS coordinates with the push of one button. See everybody queuing up for the cab stand at the end of the plaza? You don’t have to do that anymore. Use Uber to connect-the-dots between airport and rental car or hotel, or, if you’re more varsity, between light-rail hubs and rental car or hotel. Welcome to the future.

4. Trusting travel sites like Expedia or Orbitz to book hotels.

Next-in-line for most stressful travel scenario is this one: Your flight goes well, you travel seamlessly from airport to hotel, you turn the key, and surprise! The room is dirty, unrenovated, a smoking room, or in some other way not-what-you-expected. This has happened to me more times than I can count, usually in international cities like London (standards for room size are lower than in the US) and Beijing (where the room had last been renovated in the late ’80s, and was until recently a smoking room). Overseas, it can be more of a crapshoot, though I’d argue the below tip is applicable even then, but in the US, there’s no excuse for a bad hotel room.

Here’s the key – don’t trust travel sites. Do your own research. Trip Advisor is passable. Yelp is better. Local travel bloggers – trust me there are tons of us – are still better, and some combination of local articles and Yelp is best. Don’t worry about the “last minute deal” you may be missing. For some reason most of the best hotels aren’t featured on the last page of your airline package deal. You know how big a hassle it will be if you have to switch hotels mid-trip, right? Spend just an hour doing research before you leave and save yourself the headache.

Why are user-reviews more reliable? Two main reasons:

-While it’s not perfect, Yelp does a decent job of reflecting users’ real-life experiences, which often differ from the travel-site reviews or “star” ratings, which, in predictive terms, are practically worthless. Travel sites show you a narrow range of options, and in order to avoid a surprise, you often have to spend more than you should.

-If you book directly with the hotel, they assume responsibility should something go wrong. I can’t tell you how many times I’ve had an issue with a reservation I booked through a third-party site like Orbitz, and had the vendor tell me there was “nothing they could do” because they didn’t take the reservation directly. Moreover, if you like your stay, you can start a “long term relationship” with that hotel or chain, and receive special offers, know in-advance when’s the best season to book, etc.

5. Packing too much.

If this one causes you to raise your eyebrows, it’s because you’re probably not thinking through all of the “dominoes” that cascade into travel-stress when you make the simple mistake of packing too much. Let’s examine them.

-More to carry in and out of cabs, up stairs and escalators, in and our of elevators and revolving doors, etc means less flexibility and more psychological baggage.

-Most mainline carriers charge up to $50-a-bag for every item of checked luggage, and even JetBlue charges around $30 for each additional bag after the first one. That means you’re carrying extra bags onto the plane. And not just onto the plane, but through the airport, in and out of the restroom, in the line at the coffee shop, through security… When you’re waiting to board you’re sweating that somebody gets to your overhead bin before you do, and once you’re aboard you’re enduring the dirty looks of people you delay as you attempt to stuff your bulbous Tourister into the impossibly tiny empty space between a pair of ski-boots and a diaper bag, to say nothing of your feeble attempts to avoid decapitating the lady in front of you as you withdraw it before deplaning.


Repeat after me: pack the suitcase you would normally carry on the plane (or a minutely larger one) and check it. Carry on nothing that won’t fit into a small backpack. (Or, if absolutely necessary, a laptop bag. But only the laptop bag. We’re talking one total item carried onto the plane – one that will fit under the seat in front of you.)

Luggage withdrawal? What are you afraid of? Unless you’re going on a golf, fishing, or hunting outing that requires specialized equipment (that can’t be rented at your destination), what do you really need? A few changes of clothes? Makeup? A change of shoes? What are you worried you’ll forget? Your bunny slippers? Ask yourself what you would eliminate if you absolutely could take no more luggage than I recommended above.

The payoff is instantaneous. Walk around the airport like you’re gliding on air. Pass easily through security. (Well, as “easily” as possible. See below.) At boarding time, sit and read your book while everybody else is nervously standing in line, and once aboard, slip seamlessly into your seat.

6. Not using a credit card.

This is an obvious one, but I sometimes still get lazy. Everybody knows this stuff – when you’re traveling you’re more susceptible to both identity theft and actual, just-regular, theft. Credit cards make repatriating lost funds easy, whereas if somebody empties your checking account, good luck. (Also, if you ever are forced to book a rental car with one of the dinosaurs, your credit card may have insurance that covers that rental car, allowing you to opt out of the overpriced “add on” insurance many agencies try to sell you.)

7. Not setting an auto-responder on your email.

It’s astonishing how many people fail or forget to leave clear procedures in place at their job for managing things in their absence and dealing with emergencies, then spend the whole trip feverishly checking their email. (They’re easy to identify in airports.) Not only does it defeat the purpose of a vacation, responding to email on vacation also has the paradoxical effect of causing more unwelcome email, as people learn that you’re actually still “on-the-clock” on vacation. Leave clear procedures in place, inform others before you leave and again via auto-responder that you will not be able to respond to email, then don’t respond to email.

8. Putting up with the TSA.

I had wanted to put this item near the top. Few things inspire more nail-biting than today’s airport security screening. Without going into a dissertation on the TSA, you just hope you get a nice screener. If you don’t, we all know there are certain “rules” – for instance defining the maximum allowable quantity of toothpaste you’re allowed to carry-on in your “3-1-1” baggie, or mandating a user-friendly experience after opting out of a back-scatter machine – but in my experience TSA agents are under no obligation to follow them. If one decides to be a jerk, he or she can ruin your day. (If you’re reading this and you’re one of the many caring, responsible TSA employees that keeps us safe day-after-day, then 1) I don’t mean you, and 2) help your less hospitable colleagues help their own image before complaining to me:)

Then, all-of-a-sudden, there seemed to be hope, in the form of TSA Pre, a pilot pre-screening program being rolled out this fall in a limited fashion. The idea, that you pay a fee and, if you pass a background check, are allowed to pass through security with less draconian procedures, seemed like a good one. There’s just one problem – they’ll tell you if you qualify. If you’re flying with one of the participating airlines, the TSA has the option to pre-identify you based on a secret process, in which case your airline will notify you of your eligibility to participate. For the fee, of course. So the idea of you or I simply signing up like we’d apply for a passport still doesn’t exist.

Or does it?

Enter a startup called Clear Card. (ClearMe.com – no affiliation.) Clear Card sets out to do well exactly what TSA boggled hopelessly. Register online with your passport, they submit your data for you, if you’re approved you can join a shorter, gentler line. So far it’s only available at a few airports – Orlando, Denver, San Francisco, Dallas/Fort Worth, Westchester, and San Antonio – but one hopes that if they’re successful we’ll soon see them in more major airports.

For the rest of us, drawstring shorts, sandals, toothpaste and mouthwash in checked bag, and deep breaths.





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