All the digital nomad retreats and workations to know in 2020

Ever since Tim Ferriss wrote the 4-Hour Workweek, hoards of people have been firing the office and hitting the road to join “the new rich”. Life design (actively curating the kind of lifestyle you want) has taken on increasing importance. Experiences too replaced things as the pinnacle of success and somewhere along the way, the digital nomad movement took off. The more people joined the nomadic work train, the more services that cropped up to cater to them.


Specifically for those who fear that a life of location independence equates to solitude, there are countless digital nomad retreats where one may collect stamps as well as friends. Here are the digital nomad retreats, group travel programs and conferences that remote workers need to know in 2020.


*Please note that in light of the COVID-19 pandemic, these programs are subject to cancellation. Please contact organizers directly to inquire. 



digital nomad beach destinations


Hacker Paradise

Where: Medellin (Feb 2 – March 28), Montevideo, Uruguay (February 2 – 29), Rio Carnival (February 22 – 26), Florianópolis, Brazil (March 1 – April 25), Lisbon, Portugal (March 29 – May 9), Athens, Greece (May 24 – July 4), Palermo, Sicily (July 5 – August 29), Koh Phangan, Thailand (May 10 – June 6), Siem Reap, Cambodia (June 7 – July 4), Bali, Indonesia (July 5 – August 15), Kenya (August 30 – September 26), Cape Town, South Africa (September 27 – December 19), Croatian Coast (September 13 – October 24), Buenos Aires, Argentina (October 26 – December 19).


Why go: You can join programs on or after the start date.




Hacker Paradise - Digital nomad retreats

Photo credit: Hacker Paradise Facebook


Remote Year

Where: 4 months in Asia – Hanoi, Bangkok, Kyoto, Kuala Lumpur (March 1 – June 29), 4 months in Latin America – Santiago, Lima, Medellin, Mexico City (May 3 – August 9) or 12 months all around the world – Santiago, Lima, Medellin, Mexico City, Hanoi, Chiang Mai, Kyoto, Kuala Lumpur, Split, Lisbon, Valencia and Cape town (March 1 2020 – February 27 2021). 


Why go: One of the pioneers in the work and travel game and by far one of the most popular digital nomad retreats. They run tantalizing four or twelve-month rotations and you get to stay in each place for one month.




 Remote Year - digital nomad retreats in 2020

Photo credit: Remote Year Facebook


Nomad Train

Where: Moscow, Kazan, Novosibirsk, Krasyoyarsk and Irkutsk (May 18 – June 2, September 8-23 or you can choose your own dates).


Why go: The only one of this year’s digital nomad retreats on a train. This is an epic trip on the Trans-Siberian Express from Russia to Mongolia.




Nomad Train - digital nomad travel programs

Photo credit: Nomad Train Facebook


Coworking Days Pop Up Safari

Where: Cape Town, South Africa (February 6 – Mar 6)


Why go: A meeting of professionals, startups and entrepreneurs who want to stay connected for 4, 10 & 14-night coworking & coliving safari’s while finding the balance between work, life, wellness and adventure with South Africa as the setting.




Coworking safari South Africa - digital nomad retreats

Photo credit: CW Days Facebook


Work Wanderers

Where: Cape Town/ a private game lodge in South Africa (April 4 – 26), Bansko, Bulgaria (June 15 –July 5), Bali, Indonesia (October 3-25), Koh Phangan, Thailand (Oct/ Nov) and Galle, Sri Lanka (Nov/ Dec 2020).


Why go: Hassle-free travel while staying productive and working in digital nomad hotspots in premium accommodation.




digital nomad retreats and workshops



Where: The question is where don’t they go? In 2020 Unsettled will run digital nomad retreats in Bali, Indonesia (various dates every month), Lima, Peru (January 18 – February 9 and February 9 – February 16), Buenos Aires, Argentina (February 15 – March 14 and November 21 – December 19), sailing the Exumas, Bahamas (January 25 – February 1), Tuscany, Italy (various), Sacred Valley, Peru (February 9 – 16), sailing Greece (June 6 – 13), Costa Rica (May 23 – 30), Medellin, Colombia (January 11 – February 8 and September 5 – October 3), Cape Town, South Africa, April 4 – May 2 and October 31 – November 14), Barcelona, Spain (June 27 – July 25th), Tokyo, Japan (March 14 – 21), Beirut, Lebanon (May 9 – 16 and August 22 – 29), the Amazon, Peru (August 8 – 15), Playa Santana, Nicaragua (TBC).


Why go: Unsettled co-creates “remarkable experiences for professionals who refuse to settle in their pursuit of growth, meaning, and adventure”. Choose one month, two-week or one-week adventures with curated but flexible itineraries.




Unsettled digital nomad group travel programs 2020


WiFi Tribe

Where: January 10 – February 7 (Medellin, Colombia, Cape Town, South Africa and Playa del Carmen, Mexico), February 14 – March 13 (Florianópolis, Brazil, Medellin, Colombia, Cape Town, South Africa and Playa del Carmen, Mexico), March 20 – April 17 (Bocas del Toro, Panama, Lima Peru and Buenos Aires, Argentina), April 24 – May 22 (Southern Italy, Mexico City, Kyoto, Japan, Hawaii and Lima), May 29 – June 26 (La Paz, Bolivia, Barceona, Spain, Split, Croatia, Seoul, South Korea and Colorado), July 3 – July 31 (Talinn, Estonia, Medellin, Colombia, Bali, Indonesia, Biarritz, France, Calgary, Canada, and Cusco, Peru), August 7 – September 4 (Medellin, Colombia, Bali, Indonesia, La Paz, Bolivia, Edinburgh, Scotland and Kenya), September 11 – October 9 (Antigua, Guatemala, La Paz, Bolivia, Florence, Italy, Valparaiso, Chile, Istanbul, Turkey and Hanoi, Vietnam), October 16 – November 13 (Gran Canaria, La Paz, Bolivia, Buenos Aires, Argentina, Playa del Carmen, Mexico, Cebu, Philippines, Muscat, Oman and Tel Aviv, Israel), November 20 – December 18 (Buenos Aires, Argentina, Santa Teresa, Costa Rica, Goa, India and Berlin, Germany).


Why go: Every month, the group calls a new city home. On this digital nomad retreat, you’ll find a mix of passionate, wild and free, like-minded people from all corners of the world on a journey of work and travel.




Wifi Tribe Bocas del Toro retreat

Photo credit: WiFi Tribe Facebook



Coworking Unconference: Bali, Indonesia

When: March 5 – 7


About: Inspirational and aspirational speakers covering themes relating to coworking, coliving, cogiving and colearning in the magical island of Bali, Indonesia. Expect tell-alls, hot seats, experiential workshops, unique social events, curated content, and not just a parade of panels.





The Unsettled Global Summit: Sri Lanka

When: March 7 – 14


About: To celebrate their 100th experience, Unsettled is bringing their community together in one place for a special global gathering. This first Unsettled Summit has been designed as an open space to be creative, collaborative, adventurous, and completely yourself in Colombo and Kalpitiya, Sri Lanka.





South by Southwest: Austin, Texas

When: March 13 – 22


About: SXSW is the premier destination for discovery bringing together professionals from the worlds of technology, culture, music and film to celebrate what’s next with invigorating conferences, speakers and exhibitions.





Freedom Fest: Ubud, Bali

When: April 8 – 12


 About: Leaders and changemakers coming together for the first outdoor festival celebrating our freedom and human potential. Discussion topics will include new models and paradigms of living, working and being.





Running Remote: Austin, Texas

 When: April 20 – 21


About: Learn how to build and scale your remote team at the world largest remote work conference.





Nomad Sumit: Tbilisi, Georgia

When: May 22 – 24


About: Nomad Summit is the biggest conference for digital nomads, remote workers, online entrepreneurs and those who are currently dreaming about location independence and freedom. There are only 210 spots available, so book fast.




Camp Indie: Kent, Connecticut

When: June 12 – 14


About: Experiential learning without drab, stale, conference rooms. You’ll be waking up and learning in the beautiful Berkshire Mountains at “the world’s most fun conference”. Pick up the skills and make connections you need to build or grow your location independent business and travel lifestyle (all while having a blast at summer camp).





Freedom Business Summit: Kyiv, Ukraine

When: September 19


 About: Learn from worldwide top-performing lifestyle entrepreneurs the proven strategies on how to launch a wildly profitable remote business, quit the office job and turn your life into a never-ending adventure.





7in7: Cape Town, South Africa

When: October


About: Exclusively for experienced nomads (who have been location independent for over a year), 7in7 is a master plan of 7 one-week conferences in 7 countries on 7 continents. Yes, even Antarctica.





Nomad City: Gran Canaria

When: November 6 – 8


 About: Everyone should have the chance to work remotely if you feel the same join this event with hundreds of nomads from around the world.







Roam Coliving

About: Roam is a coliving and coworking community testing the boundaries between work, travel and life adventure. Starting at $500 per week, you gain access to incredible coliving spaces and local communities around the world and come and go as you please. Stay for a few nights or move in for months.


Where: Bali, Miami, Tokyo and San Francisco (London and New York are coming soon)






About: Fully-furnished apartments in NYC and DC from WeWork. There are full-time front desk attendants and housekeeping is available.


Where: New York City and Washington DC area






About: Outsite’s vision is to offer a way for people to experience the work/life integration that our generation craves with a global infrastructure that mixes physical spaces and online communities to facilitate the nomadic lifestyle.


Where: the US (Brooklyn, NYC, Oahu, Hawaii, Lake Tahoe, Austin, Texas, San Diego, Santa Cruz, San Francisco and Los Angeles) and international (Santiago, Chile, Santa Teresa, Costa Rica, San Juan Puerto Rico, Lisbon, Portugal, Biarritz, France, Ericeira, Portugal, Bali, Indonesia, Davos-Klosters, Switzerland and Tulum, Mexico).




For more coliving options, have a gander around


digital nomad destinations



Hi, I'm Rosie Bell, a location-independent writer, editor and entrepreneur. If you'd like to brainstorm ideas on life design and entrepreneurship, look no further. Let's talk right here.