Remote Year Allows You to Work and Travel the World All at Once

By Samantha Butts

Working remotely has become the reality for many people over the past couple of years, but this is not necessarily a bad thing.

Remote working can give you the opportunity to travel the world without having to take a day off.

Remote Year is a global community-based travel platform that facilitates people living, working remotely, and immersing in cities around the world.

The world’s leading remote work community was started in 2015 by co-founders Greg Caplan and Sam Pessin, the current president of the company.

An Idea Was Born

When college friends Greg Caplan and Sam Pessin worked in consulting, they often found themselves wondering why they were working behind a desk.

All of their work was done on a laptop, so they asked themselves, “why can’t we travel around the world and do it at the same time?”

This began their idea of working remotely around the world. They reached out to friends to see if they would be interested. Then Caplan and Pessin put together a simple website to collect people’s interest and applications for working remotely around the world. Quickly after launching the site, around 25,000 people applied to travel and live around the world for one year.

On that first year-long trip in 2015, they took 75 people, starting in Prague.

This was just the beginning for Remote Year. After large waves of interest and press, Caplan and Pessin launched the second program, then the third, and fourth. Each time they received around 25,000 applications.

They soon realized this was more than just a one-time thing and could be an actual business.

Remote Year, Four Programs

Since its start in 2015, Remote Year now has over 100 programs that last from one week to one year. Tue Le, the vice president of the global brand, product, and experience at Remote Year, said they believe, “in the transformative power of travel.”

The platform originally started with a one-year program, but today it offers ways for people to travel to inspiring destinations anywhere from one-week retreats to one month, four-month, or twelve-month journeys.

You bring your job, and the platform facilitates your ability to live and work remotely and move you around the world.

“Remote Year is built on the belief that travel and remote work leads to innovation, exploration, and personal and professional growth,” said Le.

One-week retreats

The one-week retreats are slightly different from the other programs. It is fully engaging and more intense than the other three.

The retreats are taken in the mindset that people are working lightly or are taking time off from their work to fully immerse in the experiences Remote Year is providing.

The one-week retreats are about reconnecting with what’s important and are centered around wellness.

They include a facilitator, accommodations, healthy chef-prepared meals, and a balanced blend of wellness activities, workshops, and local experiences.

Each retreat has a theme, usually following under these categories: wellness, purpose, or recharge.

The one-week retreat typically costs $2,200.

One-month, four-month, or twelve-month journeys

Unlike the one-week retreat, meals are not included in the one, four, or twelve-month journeys. They do all, however, include accommodations, a productive place to work, experiences, and flights in between countries.

The one-month trips allow you to discover one country, whereas the four-month and twelve-month programs enable you to travel to four and twelve countries respectfully.

The one-month trips typically cost $3,250. The four-month trips cost $12,000 and the twelve-month trip cost $32,000.

As you explore new destinations each month, Remote Year connects you with members of their global community, brings you on thrilling adventures, and allows you to grow personally and professionally through travel.

Le recommends if you can invest the time, do the longer trips. She said there is a buzz and excitement in the one-week and one-month programs. It is like the first day of school. But the twelve-month journey is a marathon.

You go into the twelve-month trip knowing it is not always going to be easy. There will be some days when you are tired and don’t want to travel.

“But those programs to me are the most magical because it’s a commitment,” said Le.

The longer programs are commitments. They are commitments to yourself, that you’re going to follow through on this journey. You are committing to the community, which becomes almost like your family.

Where can you go with Remote Year?

Remote Year has destinations in Latin America, Europe, Africa, Asia, and the United States, covering 20 countries.

This is the first year they are offering trips to the U.S., launching in four states (Illinois, Louisianna, New York, and Utah).

The platform is reopening its trips to Asia for the first time since the start of the pandemic. Le said they are also working towards expanding further into Africa. They will be entering three more countries on the continent.

A Life-Changing Experience and Sense of Community

Whether you go on the one-week retreat or twelve-month journey, Remote Year can truly impact your life. “It’s a life-changing experience for everyone,” said Le.

Much of this has to do with the community Remote Year has created with its programs. It has become a diverse group of people with a similar mindset of freedom and flexibility with this idea to define life on their terms.

Programs like this open your eyes to a new way of living that you may not have been exposed to before. They allow you to explore these places in a deeper and culturally relevant way.

Remote Year works to build and curate experiences so it is not just about moving tours around the world. It is moving people around the world who want to live and immerse in the cultures and communities they visit. The platform strays from the typical “touristy” locations.

Le said they hope to help people open their minds or eyes in a way that expands their global perspectives.

In that process, people learn a lot about themselves. They are meeting new people who expose them to new ways of thinking. They push their boundaries on who they are and what they want from life.

Le wants people to walk away after their time remote with a deeper understanding and appreciation for people from different walks of life. For people to walk away as ambassadors of the cultures and countries they travel to.

She also hopes people who go through Remote Year are able to create relationships of any kind with the people that traveled with them. Remote Year prides itself on the community it creates and the life-long memories that follow.

How to Get Started

You can easily begin your Remote Year adventure by visiting their website, Here you can explore all of the programs the platform has to offer.

You can start by looking at their programs or destinations, then by deciding which duration is best for you.

The website breaks down each program. It tells you what is included, where you will be staying, and where you will be working. The website also breaks down the price of each program.

If you want, you can speak with a sales representative who can walk you through the process, or if you feel confident, you can book the entire trip online.

Joining Forces with Venture Noire

This year Remote Year will be working with Venture Noire, a respected non-profit organization dedicated to improving Black quality of life through economic development.

Together they will launch the first international cohort of Venture Noire’s eight-week accelerator program, In the Black. This program seeks to improve the quality of life through entrepreneurship, supporting minority workforce creation and development.

This collaborative program will bring Black US-based startup founders to Cape Town and Johannesburg, South Africa to join local entrepreneurs for an accelerator program that will provide them with weekly training and mentorship on how to grow and scale their businesses.

Remote Year will be supporting the program by providing their cultural immersion experience. They will offer private local accommodations, coworking space, access to local experiences, community programming, social impact projects, health and safety resources, city and program orientations, and more.

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