How to Fly Like a Professional Globetrotter

Gear Patrol

Face it: you are an amateur flyer. You don’t need an alarm clock the morning of your flight — stress wakes you up in a cold sweat that doesn’t go away until you collapse on your hotel room bed. You leave bags behind. You settle for greasy fast food at the airport. If you miss a flight, you are inconsolable. If you’re in the emergency exit aisle and something goes wrong, the other passengers are screwed. Frankly, given the choice, and the time, you’d rather just drive.

But you are not given that choice. Best to just learn from these five men — CEOs, photographers, a buyer of green coffee — who travel as part of their job. Some are dropping 200,000 frequent flier miles a year (which is to say, they could’ve circled the globe eight times). So take your seat, fasten your seatbelt, and get ready to learn some flying tips, rookie.

Patrick Phillips

Global CEO of the Urban Land Institute

Q: Luggage: what do you bring, how do you pack? Do you check bags?
A: Never check a bag (ok, sometimes it’s essential, but avoid whenever possible); typical three-day trip means two suits in the bag, rolled or folded to reduce wrinkling, three of everything else except shoes; on the plane wear jeans or something comfortable, a lightweight sweater and/or a blazer. Topcoat only if it’s dead of winter. I swear by TUMI — a million miles and still looks like new, even if the wheels squeak.

Q: What extras (seat assignment, TSA pre-check, buying bonus airline points, etc.) are actually worth it?
A: TSA pre-check’s worth every penny, as is Global Entry; window seats if over two hours, otherwise exit row aisles if you can’t upgrade; business class essential for 7+ hours or for overnights. First class is a waste of space and money, but can be jaw-droppingly nice if you can wrangle an upgrade.

Q: How are you at handling mishaps, like delays, cancellations, missed flights? What’s your worst flying mishap story?
A: Gotta go all zen because in most cases there’s little you can do about it. The best option is to get the airline on the phone ASAP and be sweet as pie. Avoid the special services desks unless absolutely necessary. This is where elite frequent flyer status really pays off. If you’re top tier, your problem will get solved fast.

I’ve had hundreds of bad experiences, but the worst came on the shortest flight: all flights from LGA to DCA cancelled, all hotel rooms in NYC sold out, no rental cars or trains, so I ended up trying to sleep on a USAirways baggage cart, but “New York, New York” played over the PA system all night long.

Jonathan Withers

Green Coffee Buyer, Toby’s Estate

Q: What’s your routine for getting to the airport, and once you get through security?
A: In the field I try to schedule every day as productively as possible, right up through the last moments — so I’m typically in cuppings or meetings until a phone alert tells me I have to get in a cab that minute. Driving in coffee-producing countries can be terrifying, but at least you feel you’re getting there as fast as physically possible. Security as fast as possible: mileage benefits like pre-check are great domestically, but there’s no equivalent in places like Ethiopia. Just have your luggage and documents in good order, be nice to people and hope the timing works out. Gives me about enough time to maybe buy a water before boarding.

Q: What are three things you always have with you in your carry-on or checked bag?
A: Notebook & pencils, ancient Nikon with 50mm prime lens (portraits of the people involved in origin are the best coffee photos), and our two-ounce concentrated cold-brew bottles, just the right size to get through security — ask a flight attendant for hot water & guaranteed delicious in-flight coffee.

Geoff Hess

CEO, Analog/Shift

Q: What are your favorite airports/airport lounges?
A: The Virgin Atlantic lounge at Heathrow Airport — they give out lox. Heathrow has the most luxurious shopping of any airport I know, and to the extent that you spend money that you didn’t intend to, you feel better that you made it up with free smoked fish.

Q: Luggage: what do you bring, how do you pack? Do you check bags?
A: All logic dictates that I don’t check a bag. I do the complete opposite. I want to enjoy a hands-free experience in the airport, so my preference is to carry as little as possible. In truth, how many bags really do in fact get lost in transit? (Knock on wood!)

Q: Do you dress for comfort or style? Describe your standard outfit.
A: I am not a grunge airline passenger. Champion sweatpants and smoked salmon don’t go well together… But in all seriousness, an executive should not treat an airplane as his or her living room — presentable style is a must. I prefer a blazer with pockets enough for a boarding pass and passport. This also makes it easier to be taken seriously at the customer service desk when I attempt to retrieve my lost checked baggage.

Q: What’s your worst flying mishap story?
A: By far my worst mishap was a few years ago. A customs “tough guy” in Amsterdam confiscated six vintage Rolexes while I was en route to a collector gathering in the Netherlands. Trying to explain to him that my Paul Newman Daytona was nothing I ever intended to sell made me feel as though I was in the courtroom scene in A Few Good Men — he couldn’t handle the truth! Thankfully the “jury” (eventually) saw it my way.

Eric Kvatek

Fashion Photographer

Q: What are your favorite airports/airport lounges?
A: My favorite airport is probably NRT, Narita International Airport. I’ve been flying to and through Tokyo fairly frequently for twenty years and I always have a good time there. There’s a great sushi restaurant so it’s like a last chance for one more authentic sushi experience before departing.

My favorite lounge in the last few years is Turkish Airlines CIP Lounge in Istanbul. Its just incredible, it’s huge and full of amazing food and drinks. There’s a billiard table, a golf simulator and a slot-car racing track. You can get a massage! I actually check out of the hotel early to spend extra time there. It puts to shame almost any other lounge I’ve ever been to.

Q: Luggage: what do you bring, how do you pack? Do you check bags?
A: My carry on is a black Porta Brace Cargo Case. It holds a laptop, several cameras, lenses and a few vintage Harley T’s that I don’t want to risk checking. For checked luggage I use a Porta Brace Wheeled Production Case and two Patagonia Black Hole duffel bags. When my bags are full I throw several of my business cards into each bag before closing them in case the routing tag or my ID tag falls off.

Q: Do you dress for comfort or style? Describe your standard outfit.
A: I wear leather Red Wing boots, RRL jeans and a denim jacket regardless of the weather or destination. Seriously I’m not trying to be dramatic, but my theory is that you always assume your airplane’s going to crash when it’s landing. If I have to stagger through burning wreckage, metal shards and broken glass I don’t want to be wearing cargo shorts, a tank top and flip-flops.

Q: How do you get in good with flight attendants?
A: I try to be patient and grateful, make eye contact, smile. I don’t sleep on airplanes so I tend to interact with the crew more than other customers. On long international flights there’s more time to talk to them. I walk back to their little area to get drinks and if they’re bored they’ll talk. But I’m not trying to get something from them, it’s just fun hanging out with them.

Q: How are you at handling mishaps, like delays, cancellations, missed flights? What’s your worst flying mishap story?
A: I plan my schedule always assuming there will be a delay, so when it happens it rarely affects my connecting flights as I’ve allowed extra time between the segments. I don’t run in airports. If I miss a flight I just get on a later one. That said, last year a flight delay caused me to miss my own birthday party in Paris. Sometimes it’s just unavoidable and losing your cool doesn’t solve the problem.

I guess my worst flying mishap was 9/11. I was on a direct flight from Tokyo to Newark. The captain announced he was dumping all of our fuel into the Pacific Ocean and making an emergency landing in Alaska. Continental didn’t have staff at the Anchorage airport so we didn’t get moved to hotels like passengers on the other airlines. I realized all of the hotel rooms were going to be full so I got on a phone and got the last rental car in the city and one of the last available rooms. I spent two days not sure when we would get to fly and was considering driving back. In the middle of the night the airline called and said to get to the airport as soon as possible. I was on one of the only flights allowed to fly on September 13th and landed at Newark, which was completely deserted.

Frantz Yvelin

La Compagnie Founder and CEO

Q: Luggage: what do you bring, how do you pack? Do you check bags?
A: I usually only bring what I need for my trip…plus one day. I never forget a power adaptor (US, UK, etc.), my laptop for work and my tablet for leisure. Perhaps it is some “old” pilot habit but I often travel with my pilot licenses too, even if I know I am not going to fly by myself. As for packing I can confess I usually pack late, like the night right before I fly… I almost never check bags unless I go for more than a week and/or if I bring any liquid (like a bottle of wine or Champagne as a present where I go).

Q: What are three things you always have with you in your carry-on or checked bag?
A: My laptop. My tablet. A power adaptor… and some tylenol.

Q: How are you at handling mishaps, like delays, cancellations, missed flights? What’s your worst flying mishap story?
A: As everyone else, I don’t like cancellations. As for delays, that can happen to every airline in the world and I guess the most important is the information that is shared with you as a passenger and how (or how fast) you are being taken care of. If any of these show up I totally understand, but being informed, and how you are treated, are probably the most important.

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