How to get the best out of a digital nomad retreat or group travel program

Last updated on July 4th, 2024

Big fun during a Nomad Cruise workshop. Photo by Tijmen Hobbel

If you’re reading this, chances are you’re thinking of joining a digital nomad retreat or group travel program in the near future. These retreats offer the chance to explore new places, meet like-minded individuals, and find a balance between work and travel and they can be transformative experiences, both personally and professionally.


I have personally benefited from going on Nomad Cruise not once but twice in one year. I expanded my social network, picked up new skills, visited some incredible places, and also got to share my expertise with fellow nomads as a speaker. When you find the right company to join for a group work travel program, the results can be extraordinary.


But which is the right one for you, which digital nomad retreat should you join, are they enjoyable, and how can you make the most of the one?


Rosie Bell speaking on Nomad Cruise. Photo by Ronny Barthel.


Why should you go on a digital nomad retreat or group travel program?

Based on my experiences, attending a digital nomad retreat or joining a group travel program offers numerous benefits. Firstly, they help combat the isolation that is often associated with remote work, as you’ll be surrounded by a supportive community. Secondly, these programs often include curated experiences that immerse you in the local culture, offering a deeper understanding and appreciation of the destinations you visit.


Additionally, you’ll benefit from shared resources and knowledge, gain insights from others’ experiences and expertise, and get to meet remote workers (aspiring and current) who may not otherwise cross your path. Overall, a digital nomad retreat or group travel program is an excellent way to enhance your travel experience, boost your productivity, and build a global network, all while enjoying the freedom and flexibility that the digital nomad lifestyle affords.


How to get the best out of a digital nomad retreat or group travel program


1) Do your homework about the companies

Start by visiting the websites and social media pages of the companies offering the program to get a feel for their ethos, offerings, and overall vibe.


Look at their past itineraries and see if they align with your interests and needs. Companies like Remote Year, Noma Collective, and Hacker Paradise, for example, have detailed information about their programs, including the types of experiences that are up for grabs, the accommodation standards, and also the kind of workspaces provided.


Being thorough in your research can help you avoid potential disappointments and ensure you choose a program that truly fits your needs and expectations.


Noma Collective’s group travel offerings.


2) Read previous reviews

By thoroughly reading and analyzing reviews, you can get a realistic picture of what to expect and determine if a program aligns with your goals.


Look for reviews on platforms like Trustpilot and Google Reviews, on travel forums like Nomad List, and ask questions in digital nomad Facebook groups. Pay attention to recurring themes in the feedback—both positive and negative. If multiple reviewers mention the same issues, it’s likely they are legitimate concerns. On the flip side, consistent praise for certain aspects can also reassure you of the program’s quality.


Don’t hesitate to reach out directly to past participants if possible. Many digital nomads are happy to share their experiences and provide candid insights that can help you make an informed decision. Alternatively, speak to a location independence mentor who might be able to talk you through the various options of digital nomad retreats.


3) Don’t stray too far from your comfort zone

It’s all well and good to seek a challenge but you’ll be miserable on a winter mountain retreat if snow and cold don’t set your heart on fire and what you want is a slice of beach living. Similarly, don’t join a retreat where you’ll be waking up early for sunrise yoga when what you really fancy is a flexible schedule where you can set the pace. While it’s important to push your boundaries, stepping too far outside your comfort zone can lead to unnecessary stress and discomfort.



4) Know what your intention is

Be very intentional about your goals and what you hope to gain. Why are you going on this digital nomad retreat in the first place? What’s your long-term goal specifically relating to your career or traveling?


What do you want to get out of it? Do you want to forget about your busy AF lifestyle for a second? Are you a time-poor, frazzled urbanite looking to bliss out with other remote workers? Is having fun while learning something new the mission? 


While on the trip, what would you like to experience? Would you like a fusion of light work and cultural immersion or high-intensity work days merged with evening socializing?


How do you want to feel at the end of the program? If you’re going to be spending your hard-earned cash on a digital nomad retreat, you want to make sure you get what you want out of it.


Hot tub time on Nomad Cruise. Photo by Tijmen Hobbel.


5) Join the community

A digital nomad retreat is an influential period of time where like-minded people come together to share their skills, fears, hopes, ideas, and time while working on their lives, bodies, hearts, and minds. These companies are all about community-building with plenty of opportunities for socializing and networking.


Try to connect with and enjoy the other retreat companions. Join group chats, attend social events, and participate in communal activities. Nomad Cruise is known for its pre and post-trip meetups where you can get to know other participants before you arrive and spend more time with them after. Also, don’t be shy about introducing yourself and sharing your story. This openness can lead to truly wonderful connections and friendships.


Rosanna Lopes speaking on Nomad Cruise.


6) Keep a journal

Journaling can improve your mood, reduce stress, and it boosts comprehension and memory of events. During your digital nomad retreat, find the time and make a date with yourself to organize your thoughts and self-reflect. Use your journal to note down daily activities, memorable encounters, and any insights or lessons you learn along the way. This also provides a tangible memento that you can look back on in the future, reminding you of the valuable moments and lessons from your adventure.


7) Plan for downtime

Group travel programs for remote workers can be sandwiched with everything from game-changing workshops to enlightening spiritual exercises and back-to-back excursions. Burnout is real.


Schedule breaks throughout your day and don’t overbook yourself with activities. While it’s tempting to fill your schedule with activities and networking events, it’s important to plan for downtime during your digital nomad retreat or group travel program so you have the energy and mental space to take in all the beautiful things coming your way.


An unconference session on Nomad Cruise. Photo by Joanna Nolan.


Looking for a group travel program for remote workers? Read our comprehensive list of programs you can join here



Want to become a digital nomad?

If you wish to start your own location-independent business, find a remote job, learn about special digital nomad visas, or dive head-first into the world of digital nomads, book a 1:1 session with me here and ask me anything.


Where can I take courses about location independence?

On Discovery Sessions Learning, you can find on-demand courses to help you escape the rat race, travel, freelance, build or grow an online business, and maximize your freedom. Visit our course library here


What is the best travel insurance for digital nomads?

Safety Wing is the ultimate made-for-nomads-by-nomads travel insurance provider. Protect yourself anywhere in the world with their flexible nomad insurance.


How can I find accommodation as a digital nomad?

There are great deals to be found for short and longer stays (of up to 30 days) anywhere in the world on Agoda,, Expedia US, or where you can search for accommodations and filter according to criteria like desks, air conditioning, private bathrooms, and complimentary Wi-Fi.


How can I get an international SIM card when I’m traveling?

It’s quick and painless to get an eSIM (or digital SIM card) and data plan from Airalo that covers practically any country in the world before you get there so you never have to bother going into a phone shop. With the Airalo app, you can keep track of your data usage and top up easily.


Where can I find useful travel resources for digital nomads?

You can find all my nomad-friendly resources right here on this page. These will help you out whether you’re looking for the best flight search tools or digital sim cards. Also, sign up for Freedom Friday, our weekly newsletter that gives you five links with informational bites from the worlds of digital nomadism, remote work, travel, freedompreneurship, life design, and location independence. 

Hi, I'm Rosie Bell, a location-independent writer, editor and lifestyle entrepreneur. If you want inspiration and support to live, travel and work anywhere, look no further. Let's talk right here.