This Is What It Looks Like to Travel the World—While Working Remotely

Remote Year helps professionals to travel the world while working.

An Expert Guide to Traveling the World as a Digital Nomad

This could be you, living and working in Mexico City for six months then heading off to Lisbon.

Courtesy of Remote Year

We’ve said it before: Working remotely is one of the best ways to fit travel into your busy schedule. (We’ve also said that you should be taking more straight-up vacations.) While it’s an enticing thought, many are deterred by the sheer logistics of the endeavor. How do you plan your trip? Who will you travel with? How will you make sure you actually work and not let the charm of a foreign place distract you during work hours?

Those were the questions Greg Caplan was asking right before he founded Remote Year, a program that takes professionals around the globe experiencing a city each month—while still carving out time for maintaining full-time jobs. “I was traveling and working remotely myself, and wanted other people to travel with because it’s lonely,” he said. He asked his friends to join him, but they couldn’t swing it with the demands of their jobs. “I thought that there’s got to be people out there who would want to do this.” So, he created a landing page with a sign-up prompt. 25,000 applications later, Caplan whittled his group down to 75 people from 15 different countries—designers, developers, sales people, lawyers, journalists—and headed to Prague this past June for Remote Year’s first 12-city journey, which includes locales in Europe, Asia, and South America.

“We spend a lot of time choosing cities,” says Caplan. Remote Year chooses each destination based on safety, affordability, internet connectivity, and—most importantly, according to Caplan—unique cultural offerings. The total cost of this endeavor is $27,000, or $2,000 a month plus an initial $3,000 deposit, including travel between destinations, housing, some food and drink, workspace, and events. Remotes, as the individuals in the group are called, work from cafés and shared workspaces during the day, and during off time are able to explore their current city and organize group trips and events. One night, the group took boats to a secret Croatian beach for a night of dinner and drinks; another weekend saw some remotes road-tripping to Bosnia for a bridge-jumping adventure. It may go without saying, but the group skews young.

What’s fascinating about Remote Year is that it could have never existed ten—or even five—years ago. “Companies have largely moved their businesses to the cloud. People aren’t shackled to their desks anymore, and more and more places around the world have internet connectivity,” Caplan explained. “Millennials now have a different set of values, too—we believe the most important things in life are experiences. People aren’t owning things like houses and cars.”

Danielle Walsh is a former editor for Afar, based in California.
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