Remote work is not for everyone, but for many, it provides an ideal blend of flexibility and productivity that traditional office settings simply can’t provide. Both Brian and I, in particular, value the opportunity to work on the road. Workcations combine our love for travel with the practicality of earning a living. They’re perfect for disrupting the monotony of an ordinary workweek when we’re looking for a change of pace.
Work, Live, and Explore
People have different travel preferences, especially when they’re working on the road. Some might prefer to set up a temporary home base for a few weeks at a time, while others are happy to frenetically hop from one location to the next, as long as they have a reliable internet connection. Whatever your speed, there are plenty of destinations waiting to be explored.
Depending on work circumstances and visa requirements, travelers may have the ability to work remotely in different locations worldwide. Brian and I haven’t had the chance to workcation in Southeast Asia or Scandinavia yet, but they’re certainly on the list! We have, however, consistently integrated workcations into our US-based adventures. Whether it’s a west coast road trip or an Alaskan getaway, we’ve come to appreciate the freedom to work, live, and explore outside the confines of a typical 9-to-5 office job.
Top Remote Work Travel Options
Remote work travel opportunities offer a practical way to discover new destinations while maintaining an efficient work routine. They can provide access to accommodation and support services, cultural experiences, and community connections. Whether you’re traveling for a week or a year, there are options to fit your schedule and overall interests.
Full-Service Programs
Hacker Paradise
Hacker Paradise is a collective travel program for remote professionals seeking to travel while collaborating and networking with like-minded individuals.
This experience offers a full-service itinerary, comprised of a hand-selected community of 20–30 members. It includes private accommodations, co-working spaces, program activities, and two dedicated facilitators who manage all of the logistics.
Destinations vary each year but include a combination of rural and urban locations across different continents. Upcoming programs will take place in Estonia, Brazil, Costa Rica, France, South Africa, and Antarctica!
- Cost: $1,590+ for 2 weeks, $2,490+ for 1 month, or $1,990+ per month for 3-12 months
- Includes: Private accommodations, utilities, co-working spaces, professional and social activities, and two facilitators
- Participants: 20–30 members per group, typically ranging in age from their 20s to 40s
- Duration: 2 weeks to 12 months, depending on trip selection and preference
- Application Process: Video call to discuss work, goals, and ambitions to ensure compatibility
WiFi Tribe
WiFi Tribe provides a more narrow range of inclusive options in their trips, or what they refer to as chapters. Each chapter is comprised of 12 to 25 members and includes accommodations, a work space within the accommodations, and internet access.
Set itineraries are not offered, and members are responsible for their own flights, foods, and preferred activities. Participants in this remote work travel program collaborate to decide on group activities and excursions. At the same time, the program offers remote workers the flexibility to create their own schedules, allowing them to easily retreat to solitude when preferred.
WiFi Tribe is an intentional and highly curated program that requires a thorough vetting process to ensure member compatibility and create a supportive and collective environment. Wifi “Tribers” have traveled to both big cities and off-the-beaten-path destinations, including South Korea, Namibia, Poland, Italy, Chile, and Sweden.
- Cost: $490 annual membership fee plus chapters ranging from $1,200 to $2,800 each
- Includes: Shared and private accommodations, utilities, and co-working spaces within the accommodations
- Participants: 12-25 members per group, typically ranging in age from their 20s to 40s
- Duration: 4-week, 6-week, and 8-week chapters
- Application Process: Online written assessment, video interview call(s), and the MBTI personality test
Remote Work Families
Remote work travel programs aren’t limited to single and childfree professionals. They are also available to families looking to explore new destinations and diverse cultures while maintaining professional commitments.
Boundless Life
Boundless Life provides a robust solution to working while traveling with kids. It is a community-focused initiative that celebrates and promotes the dynamic intersection of education, culture, and personal and professional development.
The program is available in 6 countries and offers three-month experiences, along with shorter 3-week (December) and 4-week (July/August) cohorts for a condensed option.
The pricing accounts for fully furnished accommodations in a 1 to 3 bedroom apartment (with an option to upgrade to their Home+ selection, a premier home with outdoor space and an additional weekly cleaning), one weekly cleaning, utilities, a co-working hub, a full education program for children between the ages of 1 and 12 (with a new program set to launch Sept. ’24 for ages 13 and 14), local community teams, and weekly activities.
- Cost: It’s worth noting that families can book their own accommodations (provided there are spots still available in the education program), though booking priority is given to those who opt into Boundless Life accommodations.
- 3 Weeks (December): €500/child and €750/parent plus €1,300-€4,400 for accommodations
- 4 Weeks (July/August): €2,000/child and €600/parent plus €1,700-€9,200 for accommodations
- 3 Months (Seasonal): €1,700/child and €450/parent per month plus €1,300-€5,900 for accommodations
- Includes: Private accommodations, utilities, weekly housekeeping, education, on-site community manager, co-working space, and professional and social activities
- Participants: The program consists of over 700 families and more than 1,300 students across six destinations, each offering 15-20 apartments and education programs with class sizes limited to 18 students per class.
- Duration: 3-week, 4-week, or 3-month experiences
- Application Process: Review introduction presentation, answer online questionnaire, and schedule pre-booking call
| For a first-hand account of the Boundless Life program, check out Heath and Alyssa’s Review, which honestly details both the positives and negatives of their experience. |
Working Without Borders
Working Without Borders is a California-based travel company that organizes immersive experiences for remote workers and their families. At present, they offer two retreats for 2025: one 15-day program and one 29-day program in Peru. Costs cover private accommodations with a workspace, youth education programs, cultural activities, and a local host to assist families. Retreats are largely self-guided, with the option to participate in the community and structured activities.
- Cost: $5,440+/1 adult and 1 child for 15 days, $9,600+/1 adult and 1 child for 29 days
- Costs and coverage differ depending on available retreats
- Includes: Private accommodations with a workspace, utilities, education programs typically for kids ages 5 to 17, cultural experiences and workshops, community activities, program leaders, and a local host
- Participants: 8 to 10 families per group
- Duration: Currently 15-day and 29-day retreats
- Application Process: Online written assessment and a video interview
Nomad To Be
Families can embrace the digital nomad lifestyle with the comprehensive service packages that Nomad To Be offers from its location in Portugal. Currently, the company hosts individual families in four beautiful locations: Lisbon, Porto, Algarve, and Esmoriz. Packages can be customized to meet each family’s needs and preferences. They generally include accommodations with a workspace, a weekly cleaning, admission to a bilingual Montessori school or a private tutor for five half-day sessions weekly, cultural activities, and concierge service.
- Cost: For two adults and one child
- Esmoriz, Portugal: €4,300+ per month
- Porto, Portugal: €4,900+ per month
- Algarve, Portugal: €6,200+ per month
- Lisbon, Portugal: €8,000+ per month
- Includes: Private accommodations with a workspace, utilities, weekly housekeeping, admission to a Montessori school or access to a private tutor, cultural experiences and activities, and concierge service.
- Duration: 1 month to 12 months
The DIY Approach
Lastly, I would like to highlight my favorite and most preferred method of traveling while working remotely: The DIY Approach!
Indeed, the remote work travel programs mentioned above handle the planning, minimizing travel stress and ensuring reliable internet access. These options allow remote professionals to concentrate on their work and connect with a community while enjoying new experiences. Without a doubt, there is a market for travel experiences designed specifically for the unique requirements of remote workers.
Self-Guided Planning
However, the expense and appeal of structured travel programs may not suit those with a more independent travel style. Independent travelers often thrive on the freedom to create their own itineraries, select accommodations that align with their preferences, and connect with others on their own terms.
The DIY Approach requires curiosity and initiative. After all, travel would be considerably less meaningful without a sense of curiosity! Self-guided planning empowers independent travelers to take the reins of their experiences. It encourages lifelong learning as travelers research destinations, discovering historical and cultural insights that enrich their knowledge.
Some of the best ways to prepare for a DIY Workcation are to ensure:
- Availability of a strong and reliable internet connection.
- The most optimal location for personal preference (IE city centers, secluded retreats, historic neighborhoods, etc.).
- Proximity to desired attractions and activities.
- General understanding of the area and its customs by researching blogs, guides, online forums, etc.
- Community connections (if desired) via organic conversations, Meetup groups, or Viator experiences.
- Arrangements are made for homeschooling, tutoring, or education programs if traveling with children.
For those after my own heart, here are the DIY remote work travel options I recommend:
Housesitting
Try your hand at housesitting! Join Trusted Housesitters ($129-$259 annual fee) for access to homes all around the world. Alternatively, House Sitters America ($49 annual fee) provides access to homes only in the US. In exchange for free accommodations, housesitters agree to look after homes (and usually pets). House-sitting arrangements can vary in duration, spanning from just a few days to over six months!
Housesitters should create a strong profile, thoroughly review responsibilities, assess the provided amenities, and ask the owner plenty of questions. This creates a more seamless arrangement. Housesitting is a very personal experience, and both parties should feel comfortable establishing clear communication and setting mutual expectations.
Of course, the home should be an environment conducive to working remotely. If reliable internet is a concern, don’t forget to bring along a WiFi hotspot!
Airbnb and VRBO
Airbnb and VRBO provide a wide range of short-term and long-term accommodations. They cater to various budgets and offer an array of amenities. This competitive pricing makes them ideal for remote workers.
Not only do these rentals offer a comfortable place to stay, but they can also immerse guests in local cultures and allow them to build connections with hosts, neighbors, and other community members.
Travel Hacking
The responsible and strategic use of credit cards can unlock a world of rewards, allowing travelers to experience incredible amenities and new destinations for a fraction of the cost. Travel hacking is the practice of leveraging sign-up bonuses, loyalty programs, and strategic spending to earn free or discounted travel.
In a prior post, I outlined how Brian and I maximized our credit cards and loyalty programs to enjoy discounted rates and free stays across the country. There are lots of tips on how to “game the system,” and we’ve only scratched the surface! With responsible practice and a little knowledge, savvy travelers can find all sorts of creative and affordable ways to work on the road.
Work Remotely, Travel Often
If you’re curious about discovering new places and have the flexibility of remote work, why not try a workcation? It can be a brief trip close to home, providing a perfect opportunity to gauge the logistics and enjoyment of working remotely. The freedom to work from different destinations could surprise you, revealing a love for remote work travel that transforms how you approach your work-life balance. It certainly has for us!
There’s a lot to see and do in this world, so why not take the opportunities to do so when we can?
Have you tried any of the remote work travel options above? Which one has surprised you the most so far?
