Although Fleming has continued to travel in the Covid-19 era, she always packs masks in every bag lest one go astray. "You're always fumbling with multiple bags, and there's always a pocket with a mask in it, just in case," she says, "It's a disposable or not a disposable—whatever. There's something in every pocket."
She lives in Brooklyn, N.Y., with her partner, photographer Hans Neumann. They will be spending more time in Italy, though, where the pair is prepping their first hospitality project: Masseria Madre, which will open in early 2022, is close to the town of Ostuni in Puglia, where it sits on just over seven acres of an enduring orchard of olive trees.
Here are Fleming’s travel hacks.
If you're a frequent visitor to certain locales, this single tool will keep you sane.
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There’s a bunch of essential travel items that are, quite literally, in “to go” bags organized by continent and/or country for destinations where I frequently shoot. These containers, easily found on Amazon, are sitting in my office, ready to fly. I put local currency—both coins and notes—adapters, direct numbers of local drivers, any metro cards, and the occasional business card of a restaurant I liked on the last trip. These bags get tossed into my carry-on and are ready to crack open upon landing, right in the front of a rolling case.
Always double-check whether that window seat actually comes with a window.
Personally, I like to look out the window, because I like to see where I'm going and when I'm landing. On more than one occasion, I've ended up in a seat that had no window, and was a bit bummed because it was a flight that was longer than a couple of hours, like New York to LA. This issue seems [mostly] to affect flights within the U.S. on medium-sized jets. So I always check one article on the Points Guy, which is about configuration and flying and has a few call-outs on window seats that actually don't have windows. If you’re an avid window seat passenger, then it's worth checking your plane seat configuration online. (SeatGuru is a great resource.) Not all window seats are equal.
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She stumbled on one of her favorite new destinations while on a work trip last fall.
I was in Alaska on a job [last year], and we stumbled on Talkeetna, this very cute little town that's like the Woodstock of Alaska. And it's the base point for anyone going up to Denali. I use Talkeetna Air Taxi, who have an impeccable safety record. They are based out of Talkeetna, also home to Denali Brewing Co.—worth a visit for a pint. My go-to no-fuss accommodations is where the climbers sleep, Swiss Alaska, which isn't overly “bourgie.” There are a handful of Airbnb lodgings available with a bit more polish, like Belle's Cabin.
If budget is no concern and you want to get up to Denali, try the Sheldon Chalet,, which is nestled deep in the national park, accessible only by helicopter. The landscape in Alaska is truly phenomenal. Go in shoulder season—like June, when you won't be battling the same crowds as in July or August to get reservations. And everyone's a bit more relaxed at the top of the season, much friendlier and more welcoming. Two canny ways to hack the hassles of budget airline carry-on restrictions.
In Europe, there's a weight and size consideration, where you have to drop your [carry-on] bag in a size bin; they can be quite strict. So I usually wear a very roomy trench coat when I travel, with lots of pockets where you can hide things—not when you go through security, but when you're at check-in or the gate. I have a very nice Isabel Marant trench, which is lightweight, with internal and external pockets—sort of oversized. It has a little extra room in your pocket, maybe for a lens on each side? I also make sure my bags are like Russian dolls for the same reason, where there's a bag inside a bag that becomes a smaller shoulder bag. You might be forced to check a rolling bag at the gate, but it ends up almost empty, because you can keep your cameras with you. It's an extra bag for your precious things. Can't find the must-buy shoe back home in New York? Try that beachfront boutique instead.
If you want that cute little Jil Sander bag that's sold out everywhere—and it's not available—try a multibrand boutique somewhere like the Greek Islands or the Amalfi Coast. It's those semi-”bourgie,” high-traffic vacation destinations that might not have an actual standalone boutique for a brand but [might] stock some labels. I was in Santorini, and that happened. You might get lucky, too, and find a shoe or clutch that's otherwise sold out in the more major city boutiques at Love Me Santorini. It's quite a nice surprise to be spoiling yourself. This bag is the ultimate discreet, hands-free travel companion.
I don't travel with a Rimowa: The brand is beautiful and it's elegantly made, but I also think it makes you a beacon, or a target [for theft]. A few years ago, I changed out my carry on luggage to a Travelpro 21, a brand favored by airline staff. It's not the sexiest of luggage, but the four-wheel carry-on bag will continue to roll in a straight line by your side with some momentum—hands-free—while you ping off those last, urgent messages approaching your gate. It also signals to the gate staff that this bag will fit in any overhead, so no threat of your camera gear being checked at the gate. Never skimp on a budget airline ticket.
It's worth spending the extra £20 [$27] on a ticket to board first when you fly on a budget carrier like easyJet or Ryanair. Remember, you're on a budget airline, so there's a little bit of shuffling and elbow room as you're all trying to board as quickly as possible. So if you have the option to get there ahead of everyone, relax and have no issue or hassle with what you might be carrying. I think it's valuable. I think it's a small amount of money for the kind of return. Just have one less cocktail when you go out that night. Even if you're not entitled to compensation for any flight-related problem, it's always worth asking.
We had an instance only about eight days ago where we had a six-hour delay. So myself—plus my three people that were traveling with me—we each received just the courtesy 15,000 miles from Delta. Just make the call and ask. Once we did land, I got in touch: Be polite and call in and explain the situation. Airlines are quite receptive to keeping travelers happy (and frequently using them). Just do it in the Uber between your airport and the hotel. Why not try to add more miles to that trip?
