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The New Gap Year: Travel the Globe While Working Remotely — All Ages Welcome!

Unfortunately, gap years weren’t a thing in the ’90s when I graduated. And I have regretted never living or working abroad most of my adult life. So last year, at age 43, I threw that regret out the window and moved to Portugal.

Living in Lisbon is a dream, but moving solo to a new continent is not for the faint of heart. Which is why a new breed of age-blind companies that offer a low-risk taste of the gap year life is a very welcome development. Dust off your passport. Here are some of our favorite options.

Selfie image of Fernando Palacios with a bridge in the background

Fernando Palacios

“I needed time away from everything — but in the middle of something. I ended up sharing a flat with a 64-year-old farmer from the U.S. He was the best, even though we were different as day and night.” —Fernando Palacios, social media adviser, on his Unsettled month in Porto, Portugal, at age 45.


Digital Nomadism — Lite

The Basics: One-month or two-week co-working and co-living retreats around the world. Unsettlers work on their own projects, attend cultural immersions and lead each other in workshops on everything from branding to meditation.

Some Numbers: Founded in 2016, Unsettled has hosted 800-plus participants from 70 countries. Groups consist of 15 to 25 people. The median age is late 30s, but — wait — Unsettlers have ranged from 19 to 74!

Who Goes: “The Unsettled experience is designed around a specific life moment, not one demographic. In fact, that diversity — of age, background and profession — is what makes the experience unique,” says cofounder Jonathan Kalan. “We've had CEOs and CMOs, and farmers, architects, scientists, rare book collectors, illustrators, poets and programmers. They share the desire to ask the question: ‘What next?’ ”

What if You Have an Actual Job? Unsettled helps participants convince their boss of the value of breaking out of their routine for a sabbatical or remote-work situation. It also works with companies that want to offer more creative sabbatical and remote-work programs.

How Are the Digs? “Space that feels like home,” says Kalan, such as a large villa in Ubud, Bali, and several “not luxury but comfortable” group houses in swish Palermo Soho in Buenos Aires. They have private rooms and bathrooms.

How Much? Generally, between $2,000 and $3,000 per month, depending on the city.

Your Thing? Unsettled offers a way to dabble in nomadism way beyond your 20s. Their short trips emphasize cultural immersion and fun. Diverse groups lean toward creatives.

Selfie of Melissa Gold in the desert

Melissa Goad

“The trip gave me back things I lost over the years. I find my mind more flexible, and I have faith in my ability to figure anything out, anywhere I go.” —Melissa Goad, 47, senior finance director, on her Remote Year experience with cohorts in a Moroccan desert.

Remote Year

Changing Your World — Every Single Month

The Basics: A full year of digital nomadism, co-living with a like-minded people in a new city each month. (A four-month version was recently added.) Remote Year takes care of logistics such as flights, accommodations, co-working spaces and SIM cards. “We want you to be able to show up in a new city and jump right out of your comfort zone into a world of possibility,” a spokesperson says. Programming includes professional development, personal growth and cultural experiences.

Some Numbers: In 2014, the founders asked online: “Who wants to travel together for a year while working remotely?" More than 1,000 people signed up the first day. The median age is around 35, with some participants older than 65.

Who Goes? Participants vary in cultural background, profession, life stage and levels of education. All folks need is the ability to work remotely — not necessarily working outside a traditional office, but just that their work could happen via phone or online.

What if You Have an Actual Job? Many participants are full-time employees of traditional businesses. Remote Year helps them negotiate remote-work agreements.

How Are the Digs? Apartments in safe, popular neighborhoods.

How Much? $5,000 for the first month; $2,000 for each of the next 11.

Your Thing? With Remote Year, you don’t have to necessarily quit your job. And you won’t be surrounded solely by age 20-something start-up freelancers. All age groups are welcome. 

Hacker Paradise

Business Boot Camp on the Road

The Basics: Six- to eight-week retreats with a focus on work and professional development. A spokesman likens it to freshman year: Weekly recurring events include goal setting, skill sharing and target hitting. The focus is definitely on work; expect to spend 60 percent of the time working versus 40 percent socializing.

Some Numbers: Hacker Paradise was founded in 2014, and has led 30 retreats in 20 countries across five continents. The core age is between 27 and 37, but they’ve had participants as young as 18 and as old as 58.

Who Goes? “Hacker” can also apply to life hacks — it’s not just for techies but for anyone who can work remotely and wants to enhance productivity and creativity. Products and companies launched out of Hacker Paradise include The User Is Drunk, The Things Network and Threat9.

What if You Have an Actual Job? You’re pretty much on your own, although you can tap into their alumni community for advice about talking with HR. Hacker Paradise caters to entrepreneur types.

How Are the Digs? A hotel suite or a two- or three-bedroom apartment. Everyone (except couples) gets a private room.

How Much? Around $2,100 a month, though the price goes down if you stay longer.

Is It for You? Hacker Paradise is optimal for people who need some ass-kicking and is the younger bootcamp of the bunch. The alumni network can provide career advice and lead to work opportunities.


So many different ways to work, see the world, shake things up and get out of the rut of humdrum daily life. No backpack or hostels required!

Ann Abel is an American travel writer living in Lisbon. She has written about 86 countries for publications including Forbes, Departures and Condé Nast Traveller.