Ages: Ranges from 22-72 years old, with a median age of 33-34

Size: 30-50 people per trip

Trip duration: 4, 6, or 12 months

Caplan says that at the most basic level, the value proposition of Remote Year is making it easier to stay productive while traveling. That way, you can spend more time experiencing a place and connecting with others across other cultures, rather than looking for accommodations, travel options, and a café to work from. "We’re not satisfied with simply being a logistics provider — we strive to continually innovate and grow our platform to help drive our mission forward,” Caplan says.

Caplan says folks who travel together through Remote Year form a special bond that lives on through meetups, events, and destination houses via their community Remote Nation, which consists of over 2,000 people who have completed a Remote Year program.

Ages: Mainly mid-30s to early 40s, though people from 22-75 have participated, too

Size: 12-20 people per trip

Trip duration: 1-4 weeks

Jonathan Kalan, co-founder of Unsettled, tells Bustle that programs like Unsettled can help give remote workers a much better sense of balance, how to avoid burnout, and ways to be more productive. “It’s about making your work ‘work’ best for you, and not trying to fit into a generic one-size-fits-all model of modern office work that is only a few decades old,” he says.

While he says it’s easy to go off and travel solo as a digital nomad, at some point, either when you’re just starting out, or when you’ve been doing it long enough to realize that who you spend your time with becomes one of the most important things in travel, that’s when group programs for remote workers really bring meaning and value.

“Semi-structured experiences like Unsettled give you the ability to learn, grow, and network with people from around the world who share a similar set of values, lifestyle choices, and world view while still giving you the flexibility to live independently,” he says.

The company has also been running coworking retreats for creatives, entrepreneurs, and working professionals since 2014. “We’ve been running retreats long enough to see a lot of companies in the space come and go, and ultimately it’s our deep focus on quality, curation and connection of the community, and experience design (i.e., all things to do when you’re not working!) that have kept people coming back and living Unsettled several times a year.”

Ages: 20-40 (although they accept anyone 18+ who is able to work remotely)

Size: 7-15 people per trip

Trip duration: 2 weeks-2 months

Andrae Smith, CEO and founder of Work Wanderers, tells Bustle the main drawback of remote work is that people tend to feel lonely and isolated. She says that if people want to travel, too, they may be unsure of where to go and how to find community in a new environment. “Work Wanderers aims to solve this by offering a community-driven experience where like-minded people from all over the world live and work together while exploring a new city,” Smith says. She says that being in an environment with people who are similar in how they work encourages their Wanderers to remain focused and driven, which allows more time for enjoyment once all the work is done.

“Not only is this a place for friendships to form, but we also to focus on career development and collaboration between participants — we offer weekly Masterclasses where skilled professionals teach our Wanderers about a new skill or offer a practical workshop,” she says.

Plus, she adds, their peer-driven skillshares explore what Wanderers have to offer and encourage learning and growth. “Collaboration between participants occurs naturally as we foster an environment for innovation,” she says. “Our retreats immerse our Wanderers in the culture of the area and how to give back to local communities.”

Ages: Early 20s-70s, with 21 being the minimum age requirement and mid-30s being the average age of participants. Couples and children are also welcome to participate.

Size: 3-10 people per trip

Trip duration: One month (though some are one week)

Ann Davis, founder of Venture with Impact, tells Bustle that working remotely gives someone travel flexibility, saved time on getting to work, and also gives them a healthy work-life balance. “The mission of Venture with Impact is to expose professionals to new cultures, people, and ideas so that they may be more informed and empathetic world citizens, and in the process, provide a positive social impact,” she says. The company organizes the trip, accommodation, provides 24/7 local support, and a coworking space so that their participants can focus on cultural immersion through local events and activities. “Plus, they can focus on their custom pro-bono project in which they utilize their specific professional skills and interests to help a local organization,” she says.

“We are the only program of its kind that is centered around skills-based volunteering,” Davis says. She also says Venture with Impact is not limited to remote workers, but also for people who are interested in taking time off or working part-time for their job. “This allows for a more diverse group of participants, including teachers, university professors, engineers, social workers, physical and occupational therapists, and so on,” she says.

Ages: 25-40, give or take

Size: Around 20 people, definitely under 30, per trip

Trip duration: About 2 months (though some are less)

Spencer Jentzsch, CEO of Hacker Paradise, tells Bustle that people are becoming more and more disenfranchised with traditional employment incentives and acquiring “stuff.” Instead, he thinks the trend is toward seeking out life experiences that mean something.

Unlike being a digital nomad and traveling on your own, Hacker Paradise aims to help people form meaningful relationships, personally and professionally, while traveling the world. “You’ll always have someone to learn from, review your new business proposal, take a salsa class, with or co-write your witty Tinder response,” Jentzsch says. Plus, since the company takes care of all the logistics, you won’t have to worry about things like dealing with a plumbing issue in Asia over Google Translate, he says.

Jentzsch adds that professional development is a big focus for Hacker Paradise. “Our program includes inspiring talks, networking events, goal-setting sessions, informative skillshares, and workshops,” he says. And another bonus is that the company seeks to incorporate once-in-a-lifetime experiences. “We recently finished a trip to Rio Carnival, with a local facilitator showing us the ropes,” Jentzsch says. “It was something really special and goes far beyond what you’d find in guidebooks.”

Ages: 20s-40s, with mid-to-late 20s being the average

Size: Around 8 people per trip

Trip duration: 5 days, typically once a year

Kate Smith, founder and CEO of WiFly Nomads and The Remote Nomad, tells Bustle that as a remote worker, your work revolves around your life instead of your life revolving around work. “Someone should consider working remotely for the freedom and flexibility, whether it’s to travel, spend more time doing the things you love, or simply being able to go to a dentist or doctor appointment with not having to take a half-day off work,” she says.

Since becoming a digital nomad on your own can be overwhelming, Smith says that in addition to connecting you with a like-minded community, WiFly Nomads offers a step-by-step action plan for becoming a digital nomad that's specific to your skills and strengths.

Smith says the company teaches you how to earn an income remotely whereas, with most programs, you have to already have a remote job to join it. “We help you find remote opportunities based on your existing skills — we essentially teach you the skill of how to successfully find remote work or start an online service-based business,” she says.

So, if you want to take the working-remotely plunge and not do it alone, you can join a group like one of the above and have support along the way. And, to be honest, doing so from an exotic location doesn’t hurt either.

Experts:

Greg Caplan, CEO and co-founder of Remote Year

Jonathan Kalan, co-founder of Unsettled

Andrae Smith, the CEO and founder of Work Wanderers

Ann Davis, founder of Venture with Impact

Spencer Jentzsch, CEO of Hacker Paradise

Kate Smith, founder and CEO of WiFly Nomads and The Remote Nomad

Ages: 22-50, though the average age is 32-33

Size: 10-15 people

Trip duration: 3 weeks

Lavinia losub, a part-time nomad and the managing partner at Livit, an international service provider and support system for tech start-ups and entrepreneurs that Project Getaway is part of, tells Bustle that programs like Project Getaway are all about community. “Entrepreneurship — and its siblings like freelancing or side hustling — can get extremely lonely, very fast,” she says. “While I enjoy solo travel myself, accessing curated, like-minded, inspiring communities also inspires me and creates a great balance.”

They help people get stuff done, she says, and accelerate their businesses in multiple ways. During the process, they cowork and share offices in Bali at Livit Hub, and also experience things such as curated workations and retreat experiences. Although the Project Getaway brand is mostly in Bali, they also run programs in Thailand and Mauritius.

She says Project Getaway is different from other programs since they spend roughly 3-6 months curating the group, so people can truly help each other during the event, and then they tweak the agenda based on the needs of the group. They also have an all-inclusive approach, where you pay one fee and everything is arranged for you, including accommodation, meals, adventure activities, laundry, massages, and so on. “That way, you can focus on bringing your business to the next level, and relaxing — hard,” losub says.

In addition, Project Getaway Teams is a new product, so to speak, that the company is testing, that’s catered toward teams of 2-35 people who work remotely or partially remotely. “It’s an amazing opportunity to get a lot of work done, experience living in paradise, and bond with people in your team you might have never met in real life,” she says.