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How I Travel: Holly Bowling

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Imagine, as a musician staging a tour during Covid-19, you actually embraced the opportunity to perform in total isolation by creating a concert series at the most breathtaking destinations across the United States. That’s exactly what pianist Holly Bowling did when she announced plans for a groundbreaking virtual concert tour dubbed The Wilderness Sessions, featuring extraordinary solo performances filmed live at some of the most spectacular locations in the country.

"The idea for the Wilderness Sessions was born out of frustration with not being able to tour or play to live audiences due to the pandemic,” says Bowling. “After canceling show after show, I started looking for other avenues to play and launched a series of streaming concerts from my living room, but after a few months, that had run its course. We hatched the idea for a tour of audience-less shows out in the wilderness while on a hiking trip in the Sierras earlier this summer.”

The Wilderness Sessions celebrates Bowling's new solo piano album Seeking All That's Still Unsung. It began at California’s Lake Tahoe, and spanned destinations from Yosemite National Park to Utah’s famed Bonneville Salt Flats to South Dakota’s Badlands National Park. The second leg kicked off today in Casco Bay, Maine and will follow Bowling to New Mexico, Colorado and Utah. All performances will be broadcast on Bowling’s official Facebook page. As Bowling digs into her second leg of the tour, I checked in with her to talk airplane playlists, her favorite terminal and why embracing jet lag can lead to travel magic.

Holly Bowling’s Travel Intel:

My go-to airline is: Alaska Airlines. They don’t cram their seats together and they have healthy food, friendly U.S.-based customer service and an amazing loyalty program. More than anything though, I love them because they’re super reasonable about flight changes and checking oversize bags. As a musician I end up traveling with a lot of heavy gear and I appreciate not being charged a ridiculous amount of money to bring my instrument and equipment with me.

My favorite seat on the flight is: the window, so I can sleep. Also, I love seeing the cities and natural landmarks from the air. It’s easy to forgot how incredible it is that we get to casually take in the view from 35,000 feet. I try to spend some time staring out the window every flight.

My go-to in-flight beverage is: sparkling water and a glass of wine, unless it’s a morning flight. Then everything else takes a backseat to coffee.

My favorite airport/terminal is: SFO Terminal 2. I love the bright, airy feel and all the natural light. Plus there’s good food options, security moves quickly, and it never feels crowded. 

The second I get on a plane, I: wipe my seat area down and then put my headphones in. I use the same custom-molded in-ear monitors I use when I’m performing, which sound amazing and also block out just about everything else. Everything about airports and flying is better if I can turn down the noise around me. It’s like living in a little private cocoon. 

My go-to travel uniform is: a super soft hoodie and good, cozy socks. If I have those two things I can be comfortable just about anywhere. And always layers - I hate sweating or shivering through flights that inexplicably turn into either a sauna or a meat locker. 

My carry-on consists of: headphones, Kindle (I’m a voracious fiction reader), laptop, moisturizer, notebook, snacks, sunglasses, plus a reusable water bottle and a spill-proof coffee mug (I never leave home without them). 

The pieces I take EVERYWHERE are: my favorite hat, a pair of Saucony sneakers, and a Patagonia Nano-Air jacket. It’s lightweight, compresses super small and doubles as a pillow when the need for a nap strikes while traveling

My flying soundtrack is: constantly changing. I love using flights to dive into new music. It’s one of the few times in my life where I have a span of several hours with absolutely nothing else going on, and that’s the best way to listen: in a setting where I can give an album my undivided attention and listen to the whole thing in one sitting.

My favorite thing about flying is: being forced to sit still for several hours. The uninterrupted focus and lack of distractions on long flights allows me to do things that would take me far longer at home. I love to transcribe and analyze music while I’m stuck sitting in my seat. That plus a movie has made many a cross country flight pass in an instant.

The worst part about flying is: not being able to bring a cup of coffee through security on morning flights. Also, airports that don’t leave their TSA PreCheck lanes open all the time. (Looking at you, Denver and Newark!)

My one flying hack is: check the seat map a day or two before flying. I always try to snag an empty row if one appears last minute. 

The second I land, I: pop my headphones out and come back to reality.  

As soon as I check into my hotel room, I: flop down on the bed and relax. I’m usually spent after traveling.

My favorite hotel in the world is: I love anything on the ocean. But I often prefer to stay at smaller properties like airbnbs or vacation rentals if I’m traveling for pleasure.

My favorite city in the world is: San Francisco. I love coming home. Whether it’s from the air or from one of the bridges, seeing the city come into view after being away gets me every time. 

A concierge will know that I prefer: a good coffee shop within walking distance. Bonus points if there’s outdoor seating and puppies.

My favorite hotel memory is: waking up midway through a tour last year in a hotel bed with my husband and my dog - the two things I miss most when I’m on the road for long stretches. The hotel wasn’t anything special and I don’t remember where it was exactly. It wasn’t important. After a lot of time apart that year, it felt like the greatest hotel ever.

I conquer jetlag by: being willing to surrender to it if I can’t beat it. The inability to sleep on a normal schedule has led to some of my favorite moments traveling, like watching the sun come up on the walls of an ancient city in Morocco or staring out the window in the dead of night at a tiny French town washed in quiet moonlight. Also, coffee, valerian tincture, and naps.

My biggest piece of travel advice is: always carry a stash of emergency food and your favorite source of caffeine in your bag. It’s much more fun to improvise and let the day take you where it will (or easier to survive a travel delay or change in plans) if you’re well fed and happily caffeinated.

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