How to Never Be Stranded After a Canceled Flight

passengers at dubai airport
Passengers walk through a "smart tunnel" at Dubai International Airport's terminal 3 in United Arab Emirates on October 10, 2018. Photographer: Giuseppe Cacae/AFP/Getty Images

(Bloomberg) –At Bloomberg Pursuits, we love to travel. And we always want to make sure we’re doing it right. So we’re talking to globe-trotters in all of our luxury fields—food, fashion, cars, real estate—to learn about their high-end hacks, tips, and off-the-wall experiences. These are the Distinguished Travel Hackers.

Jen Rubio is co-founder and chief brand officer of Away. After stints working for Warby Parker and London-based All Saints, she launched Away in February 2016, focusing on hard-shell suitcases with lifetime guarantees. Their candy-colored silhouettes became staples at airports around the world at warp speed. At a recent Series D funding round, Away was valued at $1.4 billion.

The company now produces a range of bags and accessories, including recently introduced carry-on suitcases with built-in front pockets for items like laptops, giving travelers easy access to them.

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Rubio lives between New York and San Francisco, averaging about 200,000 miles a year—at least—in the air. Once a Delta Air Lines loyalist, reaching its Million Miler status, she now uses a variety of carriers. “American Airlines first class is hands-down the best transcon, with great seats and really good food,” she says.

She doesn’t rely on melatonin or Ambien to beat jet lag—this gizmo is much more effective.

I never travel without a small, USB-powered white noise machine from Aurola, whether it’s to drown out a hotel neighbor’s snores through paper-thin walls, or to add some sound texture to the deafening silence of a country retreat. I discovered it when we were first starting Away and I was traveling to China. I was booked in an Airbnb in Hong Kong on a very busy street. I live in Manhattan, so I’m fine with noise, but I could distinctly hear someone’s conversation outside, and I couldn’t stop eavesdropping. But that Airbnb had a white noise machine on the nightstand. I clicked “play” and slept so well that I went online and bought one the next day. It’s become my trigger for sleeping. There’s a Pavlovian quality to it: No matter where in the world I am or what kind of room I’m in, the machine turns on, and my brain instantly relaxes.

Duty-free shopping can save serious cash—if you know what you’re doing.

I’m the queen of duty-free. People think airport shopping is completely accidental, but you can strategize it to save a lot of money. If you’re looking at a pair of Gucci loafers, the difference between buying them in New York and at Gucci at London Heathrow can be $200 to $300. It’s as much as 35% off—insane! They’re not something you need urgently, so you can always wait.

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I use the Heathrow personal shopping program. You book it ahead of time, and tell them what stores you want to go to and how much time you have. Then the personal shopper meets you after security and takes you from terminal to terminal to get the stuff you need. I like it for Christmas shopping. I only found out about it because I noticed a bunch of Chinese tourists at Heathrow Terminal 3 with someone in an airport uniform. I went up to them and asked them what was going on, and they told me about it.

And this is how you really maximize those duty-free savings.

If you know you’re flying through an airport like Heathrow more than once, get a business card from any of the associates at high-end boutiques like Gucci or Chanel. Those airport boutiques have a limited selection because they don’t have a ton of space, but they can order things from any other boutique to be transferred there and hold it for you. Call or email them, then they will hold it for you and you can buy it—duty-free—the next time you fly from there. I did it when I was going back and forth between London and New York a lot.

Download this one app, and you’ll never be caught off guard by flight delays again.

Flighty is expensive for an app, like $50 per year, but somehow it knows when I’m going to get delayed before they make any announcements. If I board a flight, I might get a notification from Flighty it’s going to be 15 minutes delayed—and then five minutes later, the pilot will say the same thing.

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How never to be stranded after a canceled flight.

Remember the Three-Hour Rule: If you’re stuck on the tarmac for three hours, they have to go back to the gate and let everyone off. It will take 30 to 45 minutes to get everyone off, then maybe they’ll let you back on or they might cancel it if the crew times out. There’s uproar when that happens, but if you’re three steps ahead of everyone else, it makes everything much more decent. If you think a flight is going to be canceled, call the airline and ask them to protect you on a seat on a later flight, too. I’ve done that, where I was basically on both flights until one of them got canceled. Or you can go online while you’re sitting in your seat and book a ticket on the next flight as a backup. If your first flight is canceled, you can ask for a refund. And if you don’t need the second seat, you can cancel that for free because you booked it within 24 hours.

How to Never Be Stranded After a Canceled Flight
Image courtesy: Pixabay

Global Entry has counterparts across the world.

For places you travel to often, check to see if there’s an expedited entry program. Doing that has cut down my time in the immigration line by 90% sometimes. Hong Kong has a program where if you visit more than a certain number of times a year, you can sign up for the Frequent Visitor e-Channel. They actually have automated kiosks for immigration when you arrive and when you depart. They approve you for it, you get a sticker in your passport, and you bypass basically all of the manual checkpoints on arrival and departure.

The best in-flight amenity kit is the one you make yourself.

I’ve become very particular as I travel more. On every business-class flight, there’s an amenity kit, but I wish the products were better. So now I pack my own, full of a bunch of stuff I’ll need in-flight. It means I don’t spend the whole flight getting up, rummaging through my bags, and disturbing everyone. I pack silicone earplugs from Savears. I learned about them when I was sitting next to someone who was a sound technician. He was wearing the same earplugs on the plane that he used backstage at concerts. He said they were perfect, and now I use them for everything. I also pack rinse-free hand wash from Byredo instead of Purell hand sanitizer; it smells really good and is less drying. And I put on Barbara Sturm antipollution serum before flights. Air travel is not great for your skin, so if you can keep it clean and moisturized, you’re good to go.

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She loves this tiny Canadian surf town so much that she just bought a house there.

British Columbia is known for Whistler, but I love Tofino, a tiny surf town on the westernmost coast of Vancouver Island. It’s where my fiance [Flickr co-founder Stewart Butterfield] proposed to me. It’s hard to get to, but that’s kinda why I like it. Anyone who bothers making the effort to go, they’ll really appreciate it. You fly to Vancouver, and then there’s a scheduled floatplane service [to] Tofino Harbor. Once they started offering that, I bought a house there. The population is probably a couple thousand year-round. The climate is temperate rainforest, so it’s within the same 10 degrees always. There’s a beach, mountains, and it’s become a place for surfers, too. There’s also an amazing farm-to-table, or sea-to-table, foodie culture. I love Wolf in the Fog.

Make friends wherever you go by doing this every time you check into a hotel.

When I land somewhere, I go to the ATM and get money out. Then when I get to the hotel, at check-in I ask them to change around $40 into small bills. When you’re traveling, the ability to tip everyone you encounter when it’s called for, even in nontipping countries, goes such a long way.