Travel Tips from a Guy Who Travels Kinda Often

Flight Delays

Plenty of folks are more prolific globetrotters than me but but according to Google Maps I logged over ninety thousand miles across twenty-three trips in 2018. That’s enough to circle the globe 3.6 times. In all that back and forth, I’ve come to rely on certain products and services to make all that travel much easier. If you’re not already familiar with them, you may find one or two that could prove useful.

Flight Selection

For personal travel, I like to track flight prices before buying with Google Flights. You need to be specific about days, times and airlines, but once you identify the exact journeys you like, the service will watch price fluctuations and send email alerts when a specific fare has dropped or risen. For years I used Yapta to do this but that site has since deprecated its consumer service to focus on business travel.

Seat Selection

I used to choose my seats more or less randomly, opting for a window seat when possible but otherwise not paying much attention to the layout of the plane. After getting stuck in windowless rows or uncomfortably close to lavatories a few too many times, I started paying more attention. Now every time I book a trip, I look up that exact model of airplane on SeatGuru, which has maps and advice for nearly every seat on every plane.

Wrangling Itineraries

It’s been more than a decade since I started using TripIt and I can’t imagine taking a journey without it. Every time I make a travel booking of any kind—flight, hotel, rental car, train, whatever—I just forward the confirmation email to my TripIt account and the service automagically assembles it into a coherent, easy to read itinerary. I can view that itinerary on the web or in TripIt’s mobile app, of course, but I can also subscribe to my account’s calendar feed so that all of those plans show up in my calendar app. TripIt has gotten a little long in the tooth over the years—editing itineraries is less elegant than it could be—but it’s still a brilliant way to alleviate trip friction.

Getting through Airport Security

If you haven’t already applied for TSA Precheck, which lets you avoid the invariably longer standard lines at airport security, you’re wasting your own time. Even if you only travel a few times a year, this makes your airport experience dramatically easier. And if you travel with kids, this is a no-brainer, because it means your kids get the same privileges as you—including not having to take off their shoes, which itself can consume valuable time before your gate closes.

There’s also Clear, the privately run alternative security procedure that’s ostensibly faster even than Precheck. It uses biometrics instead of identity documents, and because it requires a paid membership, the lines are usually vanishingly short, if not non-existent. That said, I’ve never seen the point. TSA Precheck might save you half an hour or more over regular security; Clear might save you two minutes over Precheck. What’s more, Clear is available only in select airports. Don’t fall for this.


Even with as much travel as I do, I haven’t found it useful to subscribe to a wi-fi service like Boingo for on-the-ground hot spots. For in-flight wi-fi though, I usually just prepurchase a day pass via GoGo. But no matter how I get online while on the road, I always use a VPN service like iVPN for privacy—and for that matter so should you.


If you hate showing up at a party where someone is wearing the same dress as you, don’t fly between New York and San Francisco, as I do regularly, with an Away suitcase. Everyone has one. I had to put some stickers on mine (I don’t put stickers on anything) so that it wouldn’t get mistaken for someone else’s. That said, this is the best suitcase I’ve ever owned. The included battery is a fine gimmick, but the thing that really works for me is its “compression” system—a set of not particularly fancy internal straps that help you pack more into the suitcase than you would think possible. A few years ago I took a ten-day trip to Paris, Lyon, Berlin and Amsterdam with only my Away carryon, and it worked great.

My Away suitcase is particularly great because, unless I’m traveling with my family, when it’s unavoidable, I make it a policy to never check my luggage. Even in this day and age when technology seemingly keeps track of everyone and everything, luggage still gets lost routinely. It’s just not worth the risk, especially when I can just compress so much into the Away.

Toting Gear

This Mindshift zippered pouch is really intended for camera gear. But it’s so elegantly compact, with three compartments for accessories, that I’ve found it perfect for cables, power adapters and dongles (hat tip to my friend Matthew for the recommendation). It’s mostly transparent, so you can see exactly what you have and pull out just what you need. It also has room enough (and then some) for my Anker 40W 4-Port USB wall charger. Why carry several Apple wall chargers with you, as I did for years—like a dolt—when you could carry just one of these?

The cables I keep in that pouch are all secured with these basic Velcro cable ties. I’ve tried a lot of different cable management solutions over the years but these have worked out best for me. The eyelets allow you to securely wrap one end around your cable so that you don’t lose it while the cable is extended and in use. They’re also really cheap at about 16¢ each. Some Amazon reviewers complain about their quality but I’ve found mine have held up very well over time. Of course, as with all generic items for sale on Amazon, your mileage may vary.

One other item that’s come in handy many times is a mini power strip. They make these in really compact form now and they’re terrific when you find yourself low on power someplace where the one power outlet is already being used by someone else. Instead of fighting over that outlet, you can now share it, and the world becomes a tiny bit more peaceful. It’s also handy for hotel rooms where there may not be enough outlets for all your devices. The one I have isn’t quite small enough to throw into my Mindshift bag but it’s still useful enough that I throw it into my backpack.

Water Canister and Titanium Spork

If you’re mindful of avoiding disposable plastic—like one-time use water bottles and plastic cutlery—these are terrific companions to throw into your bag. I wrote about them in this blog post two years ago and I still carry them on every trip.

Getting Around

I think it’s pretty amazing that you can go to a new city for the first time and, armed with just a smartphone, make your way around town easily. As a public transportation fan, I like to take buses and trains to explore new cities. There’s no better app for that than Citymapper, which covers nearly forty cities. Like Apple Maps or Google Maps, you can punch in a destination and get routing directions, but Citymapper offers much more detailed options, especially for public transportation.

Reentry After International Travel

Thanks to an extremely petty and typically brutish decision on the part of the Trump administration, residents of New York State are currently barred from applying for the U.S. Customs and Border Patrol’s Global Entry program. This is unfortunate for New Yorkers who didn’t get around to taking advantage of Global Entry’s expedited immigration process; upon arrival you get to skip the immigration lines this long list of airports. Thankfully anyone who had already been approved for Global Entry is still able to use it.

But even if you haven’t yet signed up for it you’re almost as well off using the same government agency’s Mobile Passport Control app instead. Download it to your smartphone and enter your passport information inside the app within four hours of your arrival, and you’ll be expedited just as quickly as Global Entry users—this applies to New York State residents too. In fact, on a recent business trip, I “raced” a colleague through immigration; he used Global Entry and I used the Mobile Passport app, and we finished virtually at the same time. The Mobile Passport app is free, though to save your traveler information you need to pay the US$14.99 annual fee. That’s a decent value compared to the US$100 application fee for Global Entry, which also requires an interview that Mobile Passport does not. On the downside, Mobile Passport only works at these twenty-seven airports.

Airline Miles and Hotel Points

Aside from sticking to the same airline (Delta) and the same hotel chain (IHG), I don’t have any unique hacks for maximizing these rewards. I don’t even have a credit card that earns me points. When I started traveling as much as I do, it quickly dawned on me how distorting the game of miles and points can be—sometimes, when asked to take some unappealing trip to some location I don’t have much interest in, I will think to myself, “Hmm, but that would earn me a ton of miles.”

Having status at an airline or hotel is nice, but ultimately the personal, intangible cost is much higher than the benefit. I’d much rather be at home with my family than flying business class to the other side of the world. What I’ve come to believe is miles and points are just a metric for how much of your real life you’re missing. In fact, if you don’t travel that often and therefore don’t have much use for these products and services I’ve listed here then, well, in my opinion you’re doing it right.

Updated 3 March 2020 to include information on Global Entry and the Mobile Passport app.