What is a Workation and How to Plan One

WorkationThere’s no question that the way we view where and how we work is drastically transforming. In the wake of a global pandemic and the Great Resignation, we are reevaluating our jobs’ impact on our lives. For example, working in a daily nine-to-five office setting dressed in business casual clothing was once the norm, but times are changing fast.

The idea of a “workation” comes from deep digital nomad roots; essentially, that’s what a digital nomad aims to do. Digital nomads travel, see the world, and work from a reliable laptop surrounded by every landscape, ranging from a serene beachy shoreline to bright rainforest colors.

A workation is just what it sounds like; working while you’re on vacation. If you just let out an audible gasp regarding the ridiculousness of this concept because nobody really wants to work while they’re on vacation, give us a chance to explain what lies behind the idea of a workation and the ways in which you can make it happen.

Trust us, by the end of this article, you’ll be looking forward to your next strategically planned workation. Digital nomads have been living this way for decades, and it’s entirely possible, we promise!

  1. What Exactly is a Workation? 
  2. The Benefits & Challenges of a Workation
  3. Criteria to Consider when Planning a Workation
  4. Steps to Take When Planning your First Workation
  5. Effectively Planning your Workation

1. What Exactly is a Workation?

Technically, a workation asks that you use the precious vacation days you planned to spend beachside or tucked away in the mountains working instead. However, a workation also suggests that you don’t have to use any company-earned vacation days, permitting you to travel and work simultaneously (a concept that pertains to most digital nomads and remote workers today).

If you’re a freelancer or contract worker, you can vacation knowing that you won’t be losing time spent on client projects while you’re away. A workation is working while you’re on vacation, but it’s much more. A workation encompasses logging on and doing a job that you (hopefully) love while you sit somewhere you genuinely want to be, whether in the ocean or desert.

Sometimes a workation isn’t just about being somewhere beautiful, but somewhere different. For instance, perhaps you’ve been meaning to visit family but haven’t got the vacation days to make it happen. In this case, a workation is the perfect solution.

If you’re still on the fence about a workation actually being a holiday, let’s look at it from another angle. Even before Covid hit, most Americans weren’t taking vacations. We’ve mentioned that the traditional take on work culture has since changed, but how many times have you been on a trip with family and friends where everyone promised to unplug yet continued to check work messages and emails a few times a day?

You might as well be plugged in for your regular office hours and then enjoying dinner and a walk along the beach in the evening! Detaching from work can be difficult, especially for entrepreneurs and those with high-demand professions. The good news is, you don’t have to, because you can work during the day and vacation at night, which is the vision behind the workation.

2. The Benefits and Challenges of a Workation

As with most things in life, workations come with benefits and challenges. It’s up to you to decide if the pros outweigh the cons, which will likely be different for everyone. Regardless, let’s get into the perks and drawbacks of taking a well-planned workation.

The Benefits

Overall, workation helps employees feel appreciated and respected (and yes, this includes those who work for themselves), and most employers today lean into such opportunities for their staff. There are many benefits to a workation, besides the chance to work under a cabana while sipping an ice cold drink.

Striking a Balance

Our “plugged-in” society has us feeling more burnt out than we’ve ever been in the past, especially regarding work. Our phones are the first thing we check in the morning and the last thing we come in contact with at night.

Taking a workation allows people to unplug in the evenings without missing out on important work meetings, events, and deadlines. In short, a workation strikes the perfect balance between work and vacation.

Reduces the Pressure of Demanding Roles

Most of us are in demand concerning our jobs. Internal and external pressures can often lead to feelings of having to work all the time, often referred to as workaholic tendencies.

Those with demanding jobs are often compulsively in touch with their teams, checking in before realizing what they’re doing. Workations ensure that everything can continue to operate efficiently in the workplace while presenting complete and total relaxation once you’re off the clock.

Satisfies Wanderlust

If you’ve been on the internet in the last decade, you’ve likely heard the term “wanderlust” repeatedly. For a while, “wanderlust” appeared in every influencer’s bio across every social channel. While it’s undoubtedly a trendy word, there’s some credibility to satisfying humans’ need to explore.

A workation can help humans get out of the nine-to-five grind by changing the usual scenery and nightly routines. Anyone stuck in a rut can expand their horizons and challenge their comfort zone just by taking a workation.

The Challenges

While it’s hard to argue that working from a beautiful place and exploring that place at night could have drawbacks, workations don’t always go as smoothly as planned. It’s crucial to address these potential hiccups during the workation planning phase.

Time-Zone Differences

If you plan your workation somewhere with an entirely different time-zone than your typical work hours, you might be looking for trouble. Unless you’ve worked out the time difference with your employer or clients, you’ll want to pick a location that keeps you generally close to your home base time zone.

Poor Channels of Communication

While planning your workation, ensure that you’ve got the proper communication channels up and running. You’ll need to connect to your work without issue efficiently, and it’s crucial to run these tests before you leave. Also, arrange to visit a location that offers comprehensive internet service to digital nomads and remote workers.

Dedicated Work-Life Balance

Once your toes hit the sandy beaches of wherever you are, you might immediately lose the motivation to complete your work. While we’re all guilty of this, a workation requires you to maintain insight because the boardwalk might be calling, but you’ve got to log into work. Creating a daily work schedule before you leave can help significantly with this!

3. Criteria to Consider When Planning a Workation

Devising a successful workation means considering a few things before beginning the planning process. A workation requires a well-executed balance between working and relaxing, so if you’ve got a lot on your plate, it might not be a great time to go. Here are a few things to think about before you plan your workation.

The Right Time

Is it the right time for you to take a workation? Workations are typically extended, allowing plenty of time for the relaxation part of the trip. Working from a new location isn’t the same as working from your home, so make sure you have everything you need (a solid internet connection, your computer, and any other work supplies) to acclimate without issue.


How far do you plan to travel for your workation? Many digital nomads and remote workers no longer require clearance from their bosses to travel; some don’t have a boss other than themselves. However, distance can become an issue regarding time zones and travel time, so be aware of how far you want to go and how long it will take you to get there.

Trip Length

How long are you planning to stay on your workation? One week? Two? Just a few days? Those who work and travel full-time may settle down and work in one place anywhere from one month to one year, depending on how much they love the location. If you have a home base with plants, pets, or family to think about, your workation will be much shorter.

Generally, productive workations are about one to two weeks long, providing the time to immerse yourself in vacation-related activities while continuing to work full-time. Leaving time open for exploration is crucial, especially if your family is with you!

Where You’ll Stay

Once you’ve chosen a location, think long and hard about where you want to stay. You can select a rental (think Vrbo) or a hotel room. Depending on the length of your stay and who is coming with you, you’ll need comfort and a bit of seclusion while you work.

Since you’ll be spending a lot of time at your rental or hotel, look for everyday conveniences like a kitchen, ample bathrooms, or a nearby coffee shop to grab a cup and enjoy the unfamiliar scenery before work. Where you stay is crucial to your productivity, so pay close attention to detail while booking.

Overall, you want to ensure a comfortable, fruitful workspace while remaining close to your chosen location’s fun vacation aspects. Once you’ve established that you can get away without causing internal issues within the workplace, you can pick your spot, book it, and start making a list of things to pack!

4. Steps to Take When Planning Your First Workation

There are few things more exciting than a first workation. You’ll get to continue to make money without using up paid vacation time (if this pertains to you) while exploring a new location at night. Still, planning a workation can become overwhelming if you’ve never done it before, so here’s a little outline of steps to take to make your maiden voyage successful.

Pick Your Location

Your location will depend heavily on your work situation, especially concerning distance. Once you sort out how far you want to go, you can narrow it down and pick a spot that works for you. It helps to make a list of the pros and cons of each location, especially if you’re having trouble deciding.

When you’ve officially chosen, you can start the search for rentals, hotels or you can even try out some coliving in the area to live with other remote workers and digital nomads. Make sure that you take care to book a place to stay that’s close to any activities you want to experience.


Now that you’ve chosen a location, you can begin to incorporate your budget by determining how much you want to spend in total and the amount you plan to dedicate to a hotel or rental. Since this is a workation, keep in mind that wherever you stay should take up a large chunk of your budget. You’ll spend a lot of time there (regular working hours) so invest in a comfortable place you’ll enjoy.

Plan an Itinerary

Any good vacation as an itinerary and workations are no exception to this rule. However, you’ll have to plan your activities around your work schedule, such as hikes you want to take or restaurants you want to try. It helps to plan this out thoroughly before you leave so you don’t ignore work because the only spot left at the zipline company was during your morning meeting. Work first, activities second. When you plan accordingly, you’ll strike the perfect balance.


You’ll be working full days, so don’t forget to set some much-needed rest time amid the activities and vacation location exploration. Resting is a crucial component of any vacation, and that includes workations.

5. Effectively Planning Your Workation

Because workations can be trickier to plan than a traditional vacation (and we hope this little guide helps), tools are available to help you get the most out of the workation planning process. The idea is to maintain a vacation feel without losing too much of that work mentality that will keep you motivated to do your job.

Here are a few resources to check out:

  1. The top digital nomads retreats and workations you can’t afford to miss in 2022
  2. The top 2022 long-term retreats (1 month organized workations)
  3. Dave’s Travel Pages
  4. Work Tools for a Productive Workation
  5. An Ultimate Workation Guide + Destinations
  6. This HR Workation Resource
  7. This list of The Best Cities in the World for Remote Work

Your work and life calendars are essential tools for planning your workation as well, as they’ll assist you in knowing when you can travel and how far. Workations are becoming more common by the day, so now is the time to learn how to plan and execute one successfully!

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