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Kayla Grey, sports anchor and reporter
During the NBA season, Grey flies at least once a week. The journalist and sports broadcaster, who tries to pack “as light as possible,” typically travels with only a carry-on for trips up to seven days. “I cannot afford to lose things; but also, for me, it keeps me accountable of being very intentional about what I bring,” says Grey. Her go-to is a Samsonite suitcase that “looks like a little bullet” and “is super, super durable.” She opts for white for her carry-on and yellow for her checked luggage, “so I don’t lose it amongst all the black luggage bags.”
She also travels with a crossbody bag or fanny pack – she uses one from Nike – for keeping small items together when in transit. “It’s so much easier to get through security with it,” Grey says. “You can squeeze in your car keys, earphones, cards. … It kind of expands to the size that you need.” Additionally, she always travels with a film or disposable camera. “It’s a way to force me to be present,” she explains.
Nike slim waistpack, $25
Bruce Poon Tip, founder of G Adventures
Pre-pandemic, Poon Tip estimates that he traveled about 300,000 miles a year. Things slowed down to “next to nothing” but started ramping up again for the entrepreneur this past May. “I’m not going to travel with any checked bags for the rest of this calendar year, just because of all the airport confusion that exists right now,” says Poon Tip. He has been using Longchamp’s canvas and leather Cabin suitcase for years because of its capacity and old-school, no-frills interior. “I don’t need all the compartments and zippers and covers,” Poon Tip says.
For a personal item, Poon Tip recommends a backpack by Tumi, which can fit everything he needs on the go, including a laptop, an iPad and various cords. The two other things he always flies with are Maynards Wine Gums and antiseptic wipes. “I wipe down every seat that I sit in on airplanes now,” Poon Tip says. “There’s a huge ritual prior to sitting down of sanitizing the area, if you will – all the screens, handles and sides.”
Longchamp Cabin suitcase, $440
Tumi Brief Pack backpack, $715
Vanessa Craft, global head of lifestyle and education, TikTok
Craft’s go-to suitcases are by Away, and for any trip that’s longer than an overnight, she typically will check a bag. “I’ve been using Away for quite some time. … They’re convenient, affordable, easy to use,” she says. “I like the battery charger that comes with the carry-on that you can use to charge your phone.” For her personal item, Craft alternates between a size medium Ugg x Telfar bag and Chanel’s Gabrielle Hobo bag. “I try to have a purse big enough to hold my laptop without needing a separate laptop case,” she says.
To save time, Craft has a makeup bag that is only used for travel. “I don’t have to always repack my makeup and my toiletries every time I go away,” Craft says. “I have a bag that has travel-sized items or things that I’ve decanted into smaller, travel-sized portions that I just can grab and go, and it has everything from toothpaste to face cream.” Recently, she’s also started traveling with Apple AirTags. “I not only put one in my checked bag, but I also keep one just in my handbag in case it gets misplaced or anything like that,” Craft says.
Arren Williams, designer and co-founder of Casa Cubista
Williams travels often between Toronto and Portugal, where he lived for two years. For these month-long trips, he typically will bring a carry-on as well as a large checked bag, one that is “always preferably expandable” and “as large a suitcase as possible to max out the size,” he says. “When we pack a suitcase, usually it’s about a week’s worth of clothes, solidly, and then a few extras thrown in just for luck,” Williams says. “Then it’s about mixing and matching, heading to the laundromat when you’re away, and just making it work – and always leaving space to buy things while you’re there as well.” He recommends going to “foreign grocery stores and hardware stores and pharmacies” for “all of the best gifts.”
Williams’s must-have for flights? “I will not travel without my really good, ultra-minimal Uniqlo backpack that I picked up a couple of years ago,” he says. “It’s not jammed with logos and zippers and things – it is just perfectly simple.” For business trips, he will also pack a black nylon sports jacket – the one he owns is no longer available, but the style shown here is similar – that looks great for meetings even after being shoved into a suitcase.
Uniqlo backpack, $49.90
Theory Clinton blazer, $579
Michael Murphy, vice-president, Fogo Island Workshops & Design
Murphy, who flies for business “at least once every other week,” uses Rimowa’s Classic Cabin carry-on for trips of up to a week. “I like the leather detailing and aluminum, which makes it feel substantial and from an era when things were made of real things,” Murphy says. For his personal item, he has a 15-year-old leather duffle bag made by a friend, accessories designer Alejandro Ingelmo, that’s no longer available.
When he’s traveling, Murphy uses an app called TrainAway to help find local gyms that offer day passes. “I use that to try to get a workout in wherever I am,” Murphy says. He also recommends finding time on business trips to see things and fit in local experiences. “It’s not always possible in business situations to take some time to yourself, but I think if you can do it and search out things that are an alternative city tour or something that’s very focused on one topic, I think it can really change your feeling about work travel,” says Murphy, who has done a Graffitimundo tour in Buenos Aires and a LGBT tour of Jerusalem.
Rimowa Classic Cabin suitcase, $1,750
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