35 Things That Make Travel Suck Less

A little while back, with no particular outcome in mind, I started jotting down some of the little tricks that make my life on the road marginally easier. Two months later, the list is now long enough that I’m actively fighting off the temptation to spin up yet another travel blog. On the one hand, it seems to make more sense than a single blog entry with dozens of suggestions. On the other, we have enough travel blogs.

Anyway, for those of you who don’t travel much some of these may be useful. For my fellow frequent travelers, a lot of these will be obvious, but there may be a few things in here you missed. Either way, I share these in the hope that someone, somewhere, finds at least one of them useful.

As an FYI, all the Amazon URLs are affiliate links, mostly to see which suggestions are most useful to people.

Don’t Travel with Me

The most important rule, as my best friend “helpfully” pointed out on Twitter, is that you do not want to travel with me. He’s not the only friend that will ask me which flight I’m on in order to book something – anything – else. Poseidon hates me and everything in my life, so avoid me if at all possible.

Roll Your Clothes

Once upon a time, I thought I invented this technique, because technically I did. The only problem, as YouTube eventually revealed, is that a couple of hundred people invented it before I did. Anyway, if you’re terrible at folding clothes and/or refuse to do so, rolling your clothes will keep them reasonably wrinkle free while making them much easier to pack. Also, it’s much, much faster. If you need this demonstrated, type “roll clothes packing” into YouTube and take your pick.

Don’t Check Bags

Unless you have a very good reason – oversized equipment, you’re moving or you’re bringing home some very nice beers – don’t check bags. To paraphrase Woody Hayes, only three things can happen when you check bags and two of them are bad. So don’t.

MLC

Which brings me to the first product recommendation. Near as I can determine, I bought my current Patagonia MLC (Maximum Legal Carryon) in 2007. The bag still looks more or less like new, and in the seven years since I bought mine I’ve convinced maybe a dozen other people to get them as well. It’s the perfect size, it’s easy to pack and the backpack straps (or single D strap) are much more versatile than the roller which works perfectly in the airport but nowhere else. The MLC is, pretty easily, the best piece of luggage I’ve ever owned.

Prepare for Security

One of the easiest ways to sort rookie from professional travelers is the security line. The former will frantically begin to take apart their bag, remove their belt and shoes and so on once they hit the line. Professional travelers, however, have been doing that on their walk up. By the time they hit the line, their wallet and phone are stored, their belt and shoes are off, and their laptop is in a tray. Think about the security before you actually get there.

Store Glasses in Your Shoes

For business travel, I usually try to travel without my glasses, which I only wear for driving, or my sunglasses, as I’m sadly almost never outside when at conferences. But every so often I either need them or forget I have them on, and am stuck with them on the road. If you’re the type of person who also travels with a glasses case, you’re all set. I am not, and as a result had to baby my glasses so they didn’t get crushed. Then I started simply storing them in my shoes. Problem solved: the semi-rigid shoe protects the glasses in your bag, and you don’t have to bother with glasses cases.

Invest in Organization Gear

For hardcore travelers obsessed with weight, you’ll want to pass, but for everyone else I recommend getting some gear to help you organize – the weight notwithstanding. Whether that’s cables, cosmetics, batteries or something else, it’s nice to not have to dig through a rats nest of cables and other items to get something from your bag. Some people prefer stuff sacks or packing cubes, but I personally use a Quirky cord wrap for my Macbook charger and a Skooba cable sleeve for micro-USB cables, FitBit cable, Macbook VGA/DVI dongles, a Mophie battery, flash drive, 3.5mm line-in and so on.

Line-In Adapter

Speaking of line-in cabling, given that pretty much every rental car these days has an Aux line-in plug, there’s no sense in not carrying a 3.5mm cable with you. First of all, they’re cheap: $0.88 at present on Monoprice. Second, if you have to drive any distance, it’s nice to be able to plug in your smartphone to get turn-by-turn nav piped into the regular stereo, as well as being able to listen to whatever music, books, or podcasts you have onboard.

Audiobooks / Podcasts

Which in turn reminds me, store up on audiobooks (Smart Audiobook Player) and podcasts (Pocketcasts). They’re a great way to turn otherwise dead time in the car or airport into something productive or entertaining. I’ve been able cycle through everything from Raymond Chandler’s Marlowe novels to Mike Duncan’s History of Rome podcast while headed somewhere in the car, which is a big win timewise.

Ebooks

I held out for as long as I could, but ebooks are simply a better option for the frequent traveler. They’re lighter, easier to read on planes, always with you, and allow you to purchase virtually everything rather than what an airport has on stock. Used to be that physical books at least had the advantage in that you could read them during takeoff and landing, but the FAA finally killed that. I still very much like physical books and have no intention of getting rid of our library at home, but if you travel frequently, you might as well go ebooks now, because you will eventually anyway. In keeping with the recommended strategy of getting your hardware from Apple, your services from Google and your media from Amazon, all of my ebooks are bought through the Kindle store. I don’t, however, carry a separate Kindle device; all of my reading is done on my phone (Moto X) or tablet (Nexus 7).

Multi-port Travel Charger

Another big no-no for the lightweight travel people, I use and recommend a multi-port travel charger like the Belkin here. Most people these days are traveling with multiple devices – laptop and phone, maybe a tablet or Kindle as well – and the Belkin makes it easier to charge all of these at once, even if you have to split a single outlet with someone at an airport. They’re a bit heavy, but worth it.

Always Be Charging

With or without the Belkin, the cardinal rule for any serious traveler is ABC: Always Be Charging. You never know when you’re going to need a given device, so charging when you have outlets available is absolutely mandatory. It took me only one miserable overnight flight with a dead phone and laptop to learn this lesson; hopefully you won’t need that.

Pack an Extra Battery

Chances are, even if you’re vigilant about charging, you will at some point be in a position where your device is nearly dead and there are no available means to recharge it. In such circumstances, it’s nice to have a backup option. I’ve traveled with a Mophie external battery pack for a few years now, but if I was buying today I’d get something like this one from Monoprice. You never know when you’re going to need extra juice.

Pack Extra Cables

Whether you’re an Android or iPhone person, pack extra cables. The lifespan on them isn’t great, and eventually you’re going to need to charge your device and find yourself with a dead cable. An extra cable is a lifesaver in this case, and again Monoprice has them both for reasonable prices.

Pack Extra Headphones

In a legitimate disaster scenario – you left your primary noise-canceling headphones (we’ll get to these next) at home – make sure you’re not stuck with the horrific ones airlines hand out, or worse none at all. Keep a cheap extra set in your bag; the set that came with my original Moto X lives in my bag for just such an emergency.

Invest in Noise-Canceling Headphones

I resisted these for years, a) because they’re expensive and b) because the recommended models tended to be bulky over-the-ear types (e.g. Bose QC-15s) which can get hot and suck if you wear a hat. This was dumb. If you travel a lot, I recommend you go out right now and get the Bose 20‘s. You have no idea how loud flights actually are until you wear a set of these. The noise-canceling is absurd, they charge over micro-USB and they’re comfortable in-ear headphones. Seriously, they’re magic. Unless you’re an audiophile, in which case you’re on your own and may God have mercy on your soul.

Global Entry / Pre

Another thing I waited far, far too long to do was to get registered for Global Entry / Pre. If you travel internationally at all, spend the extra $15 to get Global Entry, and if you don’t just get Pre. It’s like traveling back in time before we became so scared of our own shadows that we thought it would be ok to virtually strip-search everyone before they fly. One pro-tip with scheduling Global Entry interviews: if your local interview location is booked way out, check places you fly regularly. Logan was a four month delay, but JFK was four weeks. But seriously, I can’t stress this enough: if you travel frequently, Pre is a life changer. Even more so if you consistently opt out of the porno-scanners for the sake of principle.

Get There Early

Pre access may get you through airport security lines more quickly, but don’t count on it. People laugh at how early I insist on getting to the airport – 90 minutes minimum for a domestic flight, ideally two hours – but I’m never stressed when things inevitably go wrong. And every so often, I’m able to catch a delayed earlier flight. There’s a school of thought that says that if you don’t miss at least a flight a year you’re getting there too early, but let’s be honest: are you really going to use that extra half hour or hour all that well? In my case, another few minutes kicking around at home are not worth the stress and hassle, so as Kottke says, to survive airplane travel, I get there early.

Be Nice to Service-people

You should be nice to people all the time, of course. But worst case, be nice to service people – whether they’re airline counter reps, your server/bartenders on the road or the people cleaning your hotel room. First, they have hard, often thankless jobs where customers are prone to taking out their frustrations on them. Don’t be that person. Second, they may or may not be able to help you when things go wrong, but they’re more likely to try if you’re calm and patient with them. And they can almost certainly make your situation worse if they choose to. I won’t name the airline, but when flying out of Chicago years ago a rep confessed that she had intentionally misdirected the bags of a customer who absolutely blew up at her without provocation. I approved of it then, and I do now. Don’t be an asshole.

Use TripIt

True, TripIt has been updated essentially zero times since they were acquired, and granted, Google Now is getting better and better at parsing travel details, but until it’s perfect, just use TripIt. If you allow it to scan your inbox(es), you’ll never have to lift a finger. All of your travel plans will be indexed and housed in one central location, so the next time the hotel can’t find your reservation you won’t have to dig through email search to produce the confirmation number.

Use Priceline

If you’re working for a big company that has negotiated rates with larger hotel chains, you can skip this one. For everyone else, it’s worth remembering Priceline’s “Name Your Price” feature when it comes to booking hotels (and possibly flights, though my schedule is never flexible enough for that). I pretty regularly save at least 40% or better off listed rates, and have approached the 60% figure they cite multiple times. There are a few catches: 1) you don’t accumulate any hotel rewards points (unless you’re nice to the receptionist and they sneak you in) for Priceline stays, 2) you don’t get to pick the actual hotel and 3) there are no refunds or cancellations. But you can save enough that it is frequently worth it. To use Priceline effectively, first check the inventory: if there are very few rooms available, don’t bother. You won’t save much. If inventory is high, however, check out biddingtraveler.com for reasonable bids for your area. Then select the highest hotel quality and narrowest geographic area you can, because if you get rejected you’ll have to expand out from there.

Collect Points

Situations like Priceline aside, accumulate points everywhere you possibly can. Make sure wherever you’re staying, flying or renting, you’re getting points for the stay. Ideally, you’re able to prioritize one carrier to maximize your points – I more or less exclusively fly JetBlue, for example, because they’re the only domestic carrier with enough leg room for someone over 6′ in coach. But even if schedule or corporate travel policies force you to diversify your spending, you may as well accumulate points while you’re doing it. If you travel enough, they do add up, even if some of the perks are modest.

Keep Track of Your Points

Odds are if you travel a lot you’re going to have more loyalty program information than you can remember, let alone track effectively. Centralizing this information in a single tracking service – I use AwardWallet, in spite of the fact that their Android app is terrible – can make your life a lot easier. Some people I know store all of their numbers in a text file in Dropbox or similar, but having AwardWallet actively track the status of your multiple accounts is useful.

Try Booking Directly

Many of us are used to booking travel through third party aggregators like Expedia, Hotels.com, Kayak and the like. But in many cases it’s worth booking your flights, hotel, and so on directly through the vendor. First because – third party aggregator prices aside – the cost may be lower. Second, many of the vendors may only reward you with points if you book directly with them. And third, they may issue you additional point bonuses for doing so. To be fair, third parties can have their own rewards program: Hotels.com gives you a free night every tenth purchase, for example (although it’s now an average of the ten night stay prices instead of a $400 night – used to be quite the loophole). But if you’re going to be traveling a lot, it’s usually worth trying to accumulate points in one place to get the higher level of service that returns.

Get on the Phone, Not in Line

Many of us today have deprecated the voice capabilities of our phone, preferring to deal with things either electronically or in person. But when you’re traveling, you’ll save yourself time and wear and tear by picking up the phone. When flights are canceled, for example, unless it’s a massive systemic issue, you’re more likely to get someone on the phone to fix things before the gate agents are able to negotiate the complicated needs of the dozens or hundreds of people in front of you in line.

Going to be Late? Call Ahead

If you’ve traveled with any frequency, you’ve probably encountered the situation where your flight is delayed and gets in very late, and by the time you show up at the hotel just ready to crawl into bed and go to sleep you discover that they’ve given your room away. You can prevent this sometimes, if not every time, by calling the hotel and letting them know that you’ll be late, but are still on the way. They’ll usually ask what time you might make it in, note that on your reservation and hold it for you until then. If they disappear into the back room for ten minutes, however, when you try and check in, you’re probably screwed. Be prepared to head somewhere else, though protocol is that they arrange your new accommodations for you.

Have Duplicate Toiletries

When I first started traveling, I simply packed my everyday razor, toothbrush and so on into a dop kit anytime I traveled. Not surprisingly, this inevitably leads to waking up somewhere without something you need. And while hotels are pretty good about having things on hand for just such an occurrence, the first time you shave with a terrible hotel supplied razor will probably be your last. Instead, I keep a fully stocked dop kit permanently in my MLC travel bag. That way, I don’t have to remember to pack anything – it’s already packed.

Keep a Bottle of Painkillers on Hand

For years now I’ve traveled with a worn small bottle of Advil in my briefcase that I keep fully stocked with Advil Liquigels. Whether it’s a sore head from a late night, a tweaked back from a long flight, you never want to wake up and be without a generic painkiller. Importantly, I leave this in my briefcase rather than my dop kit, because the former is with me far more than the latter.

Have a Routine

For everything: when you leave, what you do when you get there, where you store common items (phone, wallet), what you do when you get home, how you pack. Routine is everything, because the more you can navigate the logistics on autopilot the less you’re wasting time thinking about things you don’t have to.

Data Plans

Some people wonder how you justify the purchase of a cellular data plan for a second device (e.g. tablet), but the math is actually pretty simple. If you travel for a mere four or five nights a month, you’re looking at something close to $60 – $75 in hotel wireless fees. For $70, you can 11 GB of bandwidth from T-Mobile with no overage fees, and it will also be less saturated than the hotel network. Pair this with a tablet like the Nexus 7 which permits free tethering, and all of a sudden you have a hotspot for your laptop when you need to get something done.

SIM Cards

If you’re traveling overseas and need data, your best bet is to look around at the airport when you land. Most will have pre-paid SIMs available to give you prepaid data access; at Heathrow, for example, you can buy a 3 network SIM for £20 that will give you all the data you could use for a week or two.

Shipping Clothes

Occasionally on extended trips you may find yourself with clothing you no longer need. In such cases, I simply drop the now redundant clothing in a box at Fedex or UPS and ship it home. No sense toting around weight you don’t need to. I know some people who actually mail clothing directly to the hotels they’re staying at, but my track record with having things shipped to hotels is not great so I do this only if absolutely necessary (i.e. I’ve forgotten something).

Always Take Water When it’s Offered

Whenever you’re traveling, whether it’s a plane, an Uber, a train or even some buses, you’ll be offered water. Always take it, both because it’s good to hydrate and because you don’t know when you’ll need it later and not have access to it. Just remember to check your bag for water bottles before it goes through airport security, because they’ll have to rescan your bag if you forget one in there.

Take a Picture of Where You Parked

My worst lost car parking disasters came when I lived in Denver. I’d touch down at DIA late at night, it would have just started snowing and I’d wander up and down sprawling parking lots coatless, randomly hitting the panic button on my key to try and figure out where I’d parked. I’ve fallen out of the habit that fixed this, largely because if I lose my car in Portland it’s not nearly as hard to find it as I always park on the same level, but when I was in Denver I learned to take a picture of my spot after parking. I know some people who do this with their hotel rooms as well, because it’s easy for those to blur together. Anyway, it’s much easier to look up your location on a picture than it is to find your car in the snow, trust me.

How to Get to Sleep

This last one’s a bit weird, but bear with me. For a long time, I used to have trouble getting to sleep while on the road, whether it was from the stress of travel, the next day’s schedule or whatever. Then I stumbled on a solution, which will admittedly only work if you’re the only one in the room. Make sure you have a movie or TV show you know very well on your laptop – as in know it by heart (in my case it’s the Simpsons) – and play that at a volume just loud enough to hear with the screen dimmed or off. This will trick your brain into following the dialogue, thereby distracting it from getting spun up on other tasks, but since you already know it well you’ll tune out and switch off. I almost never remember listening to more than a few minutes of an episode before I fall asleep.

Got a travel tip of your own? Leave it in the comments.