Want to be a Digital Nomad but Not Sure Where to Start? How About Starting Here?


New office? Yes please!

I’ve written about the life of the digital nomad in the past but my focus has been more on the kinds of jobs one could do as a digital nomad and less on the logistics of making it work. For people who live this lifestyle, they need to make sure they have all the equipment they need as well as arranging for reliable internet and a work space in their destination(s) of choice. For the savvy and resourceful digital nomad, there are tons of tips out there on how to set up your global wifi, how to find a place to work, how to manage your time, etc. and that’s awesome! But….I wanted to focus on experiences available for people out there who might want to live the digital nomad lifestyle, but for one reason or another would rather have the logistics taken care of for them.

I’ll preface this article by saying that these experiences aren’t necessarily the cheapest options (although some aren’t that bad when you break down the costs). Yes, you could do it yourself for cheaper by living in hostels and seeking out free WiFi wherever you go or couch surfing. Rather, these experiences are for those of you who might be interested in trying out this lifestyle but are nervous about jumping in fully. You want the logistics taken care of for you, or you simply want to have a great group of people to hang out with while you’re traveling. Either way, keep that in mind. I’ve done a lot of research on different companies out there to bring you (and myself) this list, so hopefully you’ll find it to be a useful resource.

There are a few different programs out there that exist to provide aspiring digital nomads with an amazing travel experience without the stress and loneliness of doing it themselves. If this is something you might be interested in pursuing, read on…


This could be your office view.

Remote Year

Remote Year is a company I’ve been following for quite some time now with great interest. The program chooses between 50-80 people (you have to apply) and takes the group to 12 different cities around the world for one year, with one month spent in each city. They take care of all your transportation, flights, accommodations, and pretty much any other logistical thing you can think of for the whole year so you don’t have to worry about it. They also provide you with access to a co-working space that has all the tools you’ll need to succeed at work (internet, desk, that sort of thing). They also have volunteer opportunities, professional development opportunities, and of course the chance to make new friends and experience new cultures on the road. Remote Year is not a job provider, I should note. You’ll need to secure a remote job before you go, but in this world with our ever-increasing remote job opportunities, this is a real possibility. The Remote Year program doesn’t come cheap, however. Remote Year costs $27,000 for the 12-month program. There is a $5,000 down payment followed by a monthly payment of $2,000 for the first 11 months, with no payment due on the 12th month (USD). However, if you make decent money in your remote position, think of it as trading in your rent and utilities for travel. It boils down to $2250 USD per month, and of course you’ll want a little extra money for food and other activities while you’re out. I’m saying maybe $500 per month extra would be reasonable, so that calculates to $33,000 USD for everything you need for the whole year. There are a lot of professional level remote jobs out there that pay more than $33,000 USD per year so if this sounds like you, Remote Year might be something worth looking into. I’ve thought about doing it myself but my husband’s job unfortunately can’t be remote, and it would be tough to be away from him for a whole year. I might convince him to do this with me when we’re older, though. 🙂


Time for your lunch break!! 


Like the sound of the Remote Year program but just can’t justify spending that much money or being away for that long? You might be interested in checking out another company I’ve been following, Unsettled. It works very much the same way as Remote Year in that it’s a program for digital nomads that also takes care of your accommodations and work space, but the big difference is that the programs with Unsettled are only for one month in a select city (the city changes and you can apply for the one that interests you the most). Prices range from $1600 to $2400 for the month, depending on which trip you go on. This includes your room, workspace, airport pickup, a few meals (events), a local sim card for mobile connectivity as well as participation in events, workshops, etc. It does not, however, include alcohol, most meals, extra activities you might want to do, local transportation, or flights, so you’ll want to add the cost of that to your calculations. Still, if you’re looking for a more affordable option than Remote Year or you’re not able to get away for an entire year for one reason or another, this is a good option for you.

Surf Office

This site is less directed at individuals wanting the digital nomad experience and more at offices that want to either have gatherings for their remote team members or a working retreat for their team members. Still, I thought I should mention it in case any of you reading this happen to be business owners interested in taking their teams on an amazing trip and boosting morale, productivity, and employee happiness. Just saying. 🙂


Working in a pretty place makes you happy.

Hacker Paradise

Hacker Paradise is a site focused on providing amazing working holidays for digital nomads. Despite the name, you don’t actually have to be a web developer or programmer in order to go on these trips. They welcome anybody who has a creative progression…developers, designers, entrepreneurs, photographers, writers, architects, etc. The minimum stay is two weeks, but preference is given to longer stays (3 months is average trip length). They do different trips to locations around the world, and prices vary by location and length of stay, but it includes your work space and accommodations as well as social events, workshops, etc.


When you do one of these programs, you’ll meet a variety of talented, interesting people from around the world. 


Outsite is a site dedicated to helping digital nomads get set up with places to live and work. Their locations currently list places around California, Costa Rica, and Puerto Rico. Hawaii is coming soon, and they are constantly expanding to offer more locations. Think of them as a search engine to find a great place to stay, a beautiful coworking space, and a like-minded community as you travel and work your way around.


Meet your new coworker.

WiFly Nomads

WiFly Nomads is an organization dedicated to helping people transition into a digital nomad lifestyle. They have coaching sessions and programs dedicated to assisting people on their quest to achieve a remote working lifestyle. You can go on one of their experience trips where you can get a taste of working remotely while at the same time enjoy motivational speakers, networking events, etc. Sounds interesting!

We Roam

We Roam is another work and travel opportunity that pretty much sets you up with everything you’ll need from a work space to accommodations as well as things like professional development sessions, yoga classes, cultural events, language classes, fun excursions and more. The experience takes you to a different city each month, and you can choose how long or short an amount of time you want to stay (with a three month minimum). Prices are about $2000 per month (with a 20% discount for couples), but includes all your accommodations, work space, travel (with the exception of getting to and from your first and last destination), as well as a lot of other activities, events, and excursions. When you think of it that way, it’s really not any pricier than staying home (at least if you live somewhere damn expensive like I do).


So much better than a cubicle.

Cowork Paradise

Cowork Paradise is an organization geared towards giving entrepreneurs a digital nomad experience. If you’re a business owner, you can apply to this program and if accepted, you’ll spend an amazing month with like-minded business owners from around the world on the ever-fabulous island of Bali. You’ll have time and a great work space to keep up with your business while at the same time enjoying the amazing island, professional development opportunities, networking, and more. Sadly, they only accept 12 people per excursion and if you’re not a business owner making at least $250K in revenue, this isn’t for you (it’s not for me either…waaaah), but if this does sound like you, definitely check it out and let us all know how you liked it if you get selected to go.

WiFi Tribe

WiFi Tribe is, in their own words, a “coliving and coworking expedition around the world.” Well, I’m sold. The way it works is that each month is a “chapter” of the journey around the world. They pick a new city to call home for the month and members who have been accepted to the program are invited to each chapter if they would like to go. Memberships last one year. Pricing is $1800 per month for a private room or $1000 per month for a shared room if you only do one chapter in the year. If you do two chapters in the year, it’s $1600 per month for a private room and $900 per month for a shared room. If you choose to do 3 or more chapters in the year, pricing is only $1400 per month for a private room and $800 per month for a shared room. It’s welcome to anybody who is into travel and can work remotely, and includes all your accommodations and work space. I didn’t find mention of travel between destinations like some of the other services offer, but the prices are considerably less, especially if you’re with them long-term and sharing a room, so keep that in mind as well.


You’ll be just as productive on the road as you will be at home. More, maybe!

Project Getaway

Project Getaway is very similar to Cowork Paradise in that it gives entrepreneurs a digital nomad experience with professional development sessions, talks, networking opportunities, and plenty of time to get work done. It looks like they put you up in a pretty fabulous place for the duration of your two week or one-month adventure. Unlike Cowork Paradise, however, they don’t require a certain level of success to qualify for the program, only that you have an entrepreneurial mindset, so even if your business is just in the stages of infancy, you’re welcome in this program! Prices vary depending on the length of your stay as well as the level of luxury you choose for your accommodations, but it starts at $1950 for a two week excursion (flights not included), so if this is something you’re interested in, it’s certainly do-able.

The Remote Experience

The Remote Experience is a remote work and travel program geared towards people who work remotely and want to have an adventure! What’s nice about them is their all-inclusive program, which includes not only your room and work space, but also events, insurance, as well as your flights to and from the destination! As of now, the included flights are departing from LAX, JFK, BOS, or MIA airports, but if you’re not near one of those or not in the United States, they will work with you to apply a travel credit to your adventure as well. Prices vary depending on what you choose and what area of the world you want to travel to, but none are higher than $2000 per month and you can choose to go either for one month or to travel with them from destination to destination around the world.


You don’t need to quit your job to see the world.

Nomad House

Nomad House is another awesome company taking digital nomads around the world, one city at a time. Each 30 day trip costs around $2000, and each 15 day trip costs around $1000, so the pricing is on par with the other groups doing this sort of thing. They have different trips to various amazing locations around the world, so check them out! The cost includes housing, work space, workshops, city guides, some snacks, and some activities, but you’ll need to purchase your flights separately.


Roam is a site dedicated to helping working nomads find accommodation around the world. Sure, you could get yourself an Airbnb with wifi, but the advantage of using Roam is that the locations are coliving spaces, which means you’ll be connecting with other like-minded people during your travels. Think of it as a high-class hostel for people who have to work. They also serve as a gathering space for travelers as well as locals, hosting events, meetings, and classes, so you’ll have a more social experience and get to interact more with the community while you’re on the road.


This could be you on the weekends.

Nomad Cruise

Nomad Cruise is just what it sounds like…a cruise for entrepreneurs, freelancers, and digital nomads. For this company, it’s more than just traveling…it’s about connecting with like-minded individuals, networking, and creating new memories and experiences. While this is a cruise experience for working individuals and not a “vacation”, there is wifi available on board. However, the point of this cruise is more of a digital detox for nomads to network and learn from each other than to get some work done, so keep that in mind.

Terminal 3

Terminal 3 is another option for those of you who are interested in working and living in a different place each month. They provide accommodations, flights between destinations (but not to and from your first destination), coaching sessions, work space and WiFi, and more. The programs run for 6 months, but you can join for as little as one month or even for a year or more. They offer a 20% discount for couples as well. They also help you sort out any visas you may need so it’s as stress-free as possible. Pricing is a monthly fee of only $2,395 if you’re staying 1-5 months, and for 6 months or more it’s a down payment of $1,450 and monthly fee of $1,950.


What are you waiting for? Give it a try!

Digital Outposts

Last but certainly not least, Digital Outposts is a company that specializes in “Destination Coworking Experiences”. They host groups of remote working professionals as well as graduate students and those who have research or projects to do on “coworking journeys”. This is a great option for those of you who might not be sure if the digital nomad lifestyle is for you because they have experiences from two weeks through 2 months, so it’s a great way to try it out before you commit to the lifestyle long term. Like the others, they offer accommodations, work space with wifi, as well as other benefits like helping with logistics to make it easy for you. Current pricing listed on their site is $1295 for a two week journey, $1995 for a one month journey, or $1695 per month for two months or more. The prices are subject to change, however, depending on which destinations they travel to in the future.


Long story short…if you’re interested in trying out the digital nomad lifestyle, there are definitely options out there for you in order to help make it happen and help with the logistics. I’m interested in hearing thoughts from people who have done one of these programs or something similar, have done the digital nomad thing on their own, or have thought about doing it but haven’t yet made the leap.

I’m also interested in hearing from you if you know of any other programs like these that I neglected to mention. I’m doing this research for myself as well as for you, after all!

Or…you know, just your thoughts in general. I like chatting.








7 replies »

  1. ‘Great list Heather!

    Another great option are co-working spaces in your own city. We have loads in Berlin and perfect for people travelling through, and wanting to meet up, or need a space to work. Membership is normally about €20.00 – €30.00 per month!

    I’m also a member of “Travel Massive” which is more a social space for anybody interested in travel. I was one of the pioneer members for Berlin, but it’s great for when you’re in a new city, and you don’t know anyone and you want to meet up. Meetings are usually once a month, but you can meet individual members anytime anyone is free and available! And the international travel bloggers’ parties are great with tickets selling out in days!

    Liked by 1 person

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google+ photo

You are commenting using your Google+ account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s