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Want to Travel the World While Working Remotely? This Company Will Plan Your Trip

Updated December 7, 2015
by Jamie Cattanach
Staff Writer
work and travel

What if your workday started in a café in Buenos Aires’s famous Plaza de Mayo, and your weekend plans included dancing the tango with a handsome stranger?

A few weeks later, you might open your laptop and settle on your beach towel, overlooking the ocean on an island in Thailand.

This lifestyle is a reality for Remote Year participants, who’ve recently set out on the program’s inaugural journey.

What Is Remote Year?

The program takes a group of remote workers to 12 destinations around the world — a different one each month.

As a “class member,” you don’t need to worry about accommodations, travel between destinations or sourcing a workspace with reliable Internet. Remote Year handles all of the logistical footwork — just work, feed yourself and explore.

The program even puts on social events so participants can mingle, and hosts guest speakers and tours. It’s like summer camp for adults, for a year, in 12 different exotic locations.

But what does it take to be a remote nomad? And is it worth paying for a program when you could organize your own year of travel?

How Remote Year Works

The most obvious reason to sign up for Remote Year rather than planning a year of travel on your own is, well, that’s a lot of flights and bus trips and guesthouses to organize.

You pay a $3,000 down payment to reserve your spot, and then $2,000 per month, which gets you pretty much everything but discretionary travel and your meals.

Although the accommodations vary in each city, from university dorms to hotel rooms, you’re guaranteed to have your own room.

And some of the accommodations are very nice, indeed: Katelyn Smith of The Remote Nomad shares video footage of her digs in Cavtat, Croatia, with a private kitchen, bathroom, bedroom and free laundry on-site:

You need to already have a remote job — Remote Year isn’t an employer. If you don’t already work remotely, the program recommends asking your boss if it’s an option

Or, consider taking a side hustle full time, starting a freelance business, or finding a location-independent position a job board like Indeed or FlexJobs.

Is It Worth It?

With a total cost of $27,000 for the year before food, drinks and other expenses, Remote Year definitely isn’t a frugal way to travel.

Participant Arikia Millikan, who left the program early, traveled the world for a year as a freelance journalist before trying the program — and continues to travel solo since she dropped out. She’s visited Belgrade, Berlin and Istanbul, and says she only spends about $1,000 per month.

For Millikan, Remote Year “isn’t actually about working at all,” but is rather “a poorly executed tourism operation.”

She finds less expensive — and more productive — travel opportunities on her own, by speaking with locals in each area to find options within her budget.

Tourism is expensive. Traveling doesn’t necessarily have to be. — Arikia Millikan

But Smith says Remote Year fostered the “strongest sense of community [she’s] ever felt,” and that it “made [her] a better person.”

Her blog post on what to expect of the program cites such intangibles as traveling with a group that “gets you” and getting a crash course on the digital nomad lifestyle as worthy reasons to pay so much money for the program.

And you’ve got to admit, having all the details worked out ahead of time is a pretty nice perk.

With the changing costs of airfare based on season and location, figuring out where to go next while staying within your budget could be exhausting. Millikan admitted planning her own travel was time-intensive, estimating she spent five to 10 hours planning every transition to a new city.

Another Day in Paradise?

Though clicking through the Remote Year blog is sure to inspire jealousy (at least it did for me!), the program does come with a few drawbacks.

Although all the travel logistics are taken care of, hidden costs and at-home planning can create big headaches of their own:

  • When does your lease end? Since you don’t get to decide when your year of travel starts, you might be hard-pressed to find a subletter in time.
  • Do you have pets? Who’s going to pet sit for an entire year?
  • Which vaccines do you need, and how much will you end up paying for them out of pocket?

While almost everyone says they “love to travel,” a nomadic existence of this magnitude — and for this amount of time — is a huge commitment. In her post on Mashable about preparing to depart on the adventure of a lifetime, Stephanie Walden writes:

I’ve had more than one friend tell me, ‘You won’t come back the same.’ While I know this deep down, it makes the goodbyes sting just a little more. Something feels a little more permanent.

Even if you’re already working from home and want to take advantage of your location independence, to participate in Remote Year, you need to be comfortable with instability.

The one “solid” thing in the program, the itinerary, is liable to change — and according to Millikan, it did this year. The group ended up in Cavtat, Croatia, only after the organizers were unable to find sufficient accommodations in Dubrovnik. Cavtat is now listed on the 2016 itinerary.

That said, if you can pull it off, I’m hard-pressed to think of an easier way to accomplish so much travel for so little planning — and since you spend a full month at each destination, you have the chance to get a sense of what it’s really like to live in a given country, rather than just visiting.

And let’s not forget, the program is just getting started: Who knows what might change next year? Maybe one of our readers will find out firsthand.

Applications for next year’s program, which starts in February, are already under review — but they’re still accepting new ones, so if you’re interested, get yours in!

Your Turn: Will you apply to take part in Remote Year 2016?

Disclosure: We appreciate you letting us include affiliate links in this post. It helps keep the beer fridge stocked in the Penny Hoarder break room.

Jamie Cattanach is a junior writer at The Penny Hoarder and a native Floridian. She’s passionate about learning, literature, chocolate and finding ways to live the good life as cost-effectively as possible. You can send smoke signals (or, you know, friendly greetings) to @jamiecattanach on Twitter.

by Jamie Cattanach
Contributor for The Penny Hoarder

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