The Rise Of The "Workation"

For five months, Maya Kachroo-Levine and her husband worked 12-hour days from their house in Los Angeles. “We desperately needed a change of scenery, and we’d been fantasizing about a Palm Springs bungalow with a pool, but impulsively buying a second home wasn’t exactly in our budget,” she says.

Instead, the couple booked three separate Airbnbs in Palm Springs — one each for August, September, and October — for mini “workations.” “It’s amazing what four days a month in a different house can do for your mental state,” says the 29-year-old freelance travel writer and copywriter and freelance writer. Having a pool didn’t hurt, either.

After months of safer-at-home restrictions in response to the COVID-19 pandemic, that desire for a change in scenery has led to a rise in workations, or working vacations. There’s no one-size-fits-all approach: People are taking workations with their partners or small groups of friends, and they’re traveling for long weekends, a few weeks, or a month or longer. It doesn’t hurt that more than 33% of Americans are still doing their jobs from home and another 25% are working remotely part-time due to coronavirus, a Gallup poll reported; meanwhile, tech giants like Amazon, Facebook, and Google have announced extended WFH plans into summer 2021. In fact, 82% of companies surveyed by research and advisory company Gartner said they plan to offer remote work at least part of the time after the pandemic.

People who have the means and flexibility to work from anywhere are actively booking longer stays (two-plus week trips), recent survey data from Airbnb revealed. Hard-hit hospitality and tourism industries are also leaning into the trend. Hyatt, for example, recently launched the Work From Hyatt extended-stay package at 90 hotels across North America and the Caribbean. Internationally, Aruba Tourism Authority’s new “One Happy Workation” program allows visitors to stay for up to three months; the islands of Antigua and Barbuda’s Nomad Digital Residence program will host remote workers for up to two years; and visitors to Barbados can apply for the “Welcome Stamp” visa to work remotely on the island for up to one year.

Most remote workers, however, are simply DIYing their workations, both for convenience and safety purposes. The vast majority — 80% — of trips this fall will be road trips, according to a AAA survey, allowing for spur-of-the-moment travel decisions. (One in five people who are planning a trip before the end of this year expect to finalize their plans within a week of traveling, AAA found.)

Jenny Wang, a 30-year-old publicist based in Washington D.C., recently left the city with three friends for a workation in the sleepy rural town of Mountain Dale, New York. The four women shared a $100 a night, 700-square-foot cabin for six days.

“We started each morning with a discussion about who had an important call, who needed a private room, or who had class,” she says. From there, they coordinated their spaces (there was one bedroom, a lofted area, the main area, and outdoor picnic tables) for the workday. Since Wang’s job requires nonstop calls, she set herself up in the cabin’s tiny enclosed entryway, rolling a heater inside to stay warm and placing her laptop on a bench while sitting on the floor.

“I was a little more productive than when I was working from home alone,” she says. “I thrive being around people, and I’m not someone who’s easily distracted. It was actually energizing to be in a new space.”

"The workation was a great excuse for us all to get outside on the deck or go for a short walk. It reminded me that it’s normal not to be chained to your desk all day."

Having others around also makes it easier to set work-life boundaries, something nearly half of Americans who have been working longer hours since the pandemic started admitted to struggling with, according to a survey by JDP.

Nicole Nichols, 33, a senior director of research at a consultancy firm, and her husband left Boston for a weeklong workation with another couple in the Berkshires this August. “It was essentially an elevated work from home experience,” she says. “We’d each log on to calls and meetings every day, then around 5 p.m., we’d have happy hour and begin cooking dinner.”

Although their daily routines didn’t vary much from what they do at home, there was one welcome change: “When I work from home normally, I hardly ever take proper breaks,” says Nichols. “But the workation was a great excuse for us all to get outside on the deck or go for a short walk. It reminded me that it’s normal not to be chained to your desk all day — and I needed my friends in the next room to remind me that I deserved time away from my phone and computer.”

Finding time away from your screens is a crucial element of the workation. It’s not just about introducing a new backdrop to your Zoom calls but maximizing what you’re able to do in your off hours. For Emilie Berman, 25, a New York City based public relations and marketing coordinator at The Knot, a workation with her boyfriend was an opportunity to explore another part of the country without having to relocate.

The couple booked one-way tickets to Denver, a monthlong Airbnb in Denver — using it as a home base to visit other Colorado towns like Beaver Creek, Vail, Aspen, Boulder, and Colorado Springs — and a rental car for two months. “We’re still working East Coast hours, so we get up early, bang out our eight or so hours of work, and are done by 4 p.m. Then, we still have time to go hiking before sunset and explore whatever town we’re in at night,” she says.

After Colorado, the couple drove through Utah to see the national parks before heading south to Arizona and then west to Los Angeles. Staying on top of work on an extended trip like this can be a challenge, but that’s where PTO comes in. “Because of the pandemic, neither of us has really used a whole lot of vacation time,” says Berman. “We’ve been able to take a Friday off here or there, and recently we took a Wednesday through Friday off to go off-the-grid at a tiny home in Utah.”

Until recently, the idea of becoming a digital nomad or embracing a laptop lifestyle has been reserved for influencers and those with the most flexible work setups. But in a year that — for many people — has felt like a waste, combining business with travel is providing people with a much-needed escape. “As crazy as 2020 has been,” says Berman, “we feel really fortunate that we were able to at least make the best of a bad situation.”