Your Complete Guide to Taking a Workcation in 2021

Hands on a laptop keyboard – Why Now Is the Perfect Time to Take a Workcation

While taking a vacation might not always be in the cards for your schedule every year, there are other creative solutions to plan a bit of a getaway if you’re itching to change things up.

A workcation (also spelled workation) could be a great plan for you right now. They allow you to stay on top of things and get your work done, all while doing something you enjoy and taking some time to explore new places. It’s sort of the best of both worlds, and right now could be the perfect time to try it out.

While there is a lot to learn and prepare for when looking to take your workcation, it could be well worth it by the time you’re in your dream destination ready to go out and explore — all while feeling the productive satisfaction of a workday well done.

What Is a Workcation or Workation?

To put it simply, a workcation or workation is a working vacation, where you take a break from the workplace, but perhaps not the work itself. It’s a vacation where you can go where you please, but you do so while working remotely.

Another term that addresses this trend is ‘bleisure’, which means combining work and leisure, usually in a fancy destination.

If you already work remotely, you may have dipped your toes in this world already, like the occasional family visit or weekend away where the laptop comes with you. But if you work in an office, it could be entirely new territory. It helps create a great balance for those who need a bit of a getaway, but can’t abandon all work responsibilities right now.

Why Now Is the Perfect Time to Take a Workcation

If there’s ever been a perfect time for workcations, it’s right now. Due to the COVID-19 pandemic, plenty of people who normally would work in an office are working remotely already. Taking a workcation when you’re already working remotely takes much less mental gymnastics and is often much more feasible — although they are still totally possible for those who work in an office.

While COVID-19 has certainly created a push for more remote workers, it’s not wholly responsible for the popularity of the workcation. Simply put, technology is better than it ever has been and communication works much more efficiently. While even a few years ago getting out of the office to work remotely might have meant a productivity slump, now it doesn’t have to. With more people than ever normalizing remote work and workcations, taking one yourself could be much simpler than you expect.

From Staycation to Workcation

There are varying degrees of taking a workcation.

If you happen to be working remotely already — or you simply want to get out of the office and chill at your own abode and unwind — congratulations! You’ve got yourself a staycation. You’ve probably taken one of these before, but if you haven’t, they can be a great introduction to the workcation flow.

However, if you want to kick things up a notch, you can always take a domestic workcation by going somewhere new in your own home country or time zone to get away. This can create much less work for you in the planning process and stretch your budget so you can stay even longer.

Vacations, like going glamping, getting out into nature, or taking a road trip, are great ways to stay a bit closer to home so you can remain on your company’s schedule. They can also be great as introductory workcations so you can try it out and get a sense of your flow.

However, you could also go all out and try your hand at workcationing abroad. By going to another country, you often have to take travel time into account, adjust to a new time zone, ensure that you’re staying safe per local health guidelines, and acquire the proper visas, but the experience can make all the effort worth it. As long as you’re being safe and responsible, you should explore wherever your heart takes you.

Special Workcation and Digital Nomad Visas in 2021

Depending on the length of your getaway, you might want to look into the digital nomad lifestyle. While it might not be for you over the long term, giving it a try for a bit of a change could be the perfect way to reinvigorate your enthusiasm for your job and the world around you.

While a week-long workcation might be the most you can take on at the moment, for those with jobs that can be done remotely, more flexible schedules, and indefinite remote working situations, an extended workcation might be in the cards.

In order to stay in another country for longer periods of time, you’ll need to go through a visa process to ensure everything is aboveboard. The good news is that there are many countries that offer specific work visas for digital nomads, freelancers, and remote workers.

Whether you have your sights set on Europe, South America, or even a gorgeous island paradise, there is an array of countries that offer specific visas for people who work remotely. Portugal, Aruba, Georgia, Germany, Spain, Estonia, Barbados, Bermuda, Antigua and Barbuda, the Cayman Islands, Mauritius, Mexico, Czech Republic, and Dubai are a few places you can park your traveling office for extended periods of time.

While each country has its own specific rules and guidelines, some of these visas allow for months (and even years) of working remotely. This could even be a great way to try out living in a foreign country you might like to move to permanently one day.

What to Take Into Consideration Before Heading Out

Perhaps the better question should be, what don’t you have to consider before packing up and heading out? Especially in the world’s current health and safety situation, you’ll need to make sure your working vacation is responsible and safe before you go anywhere.

If you plan to go abroad, looking into your home country’s travel guidelines as well as those of your target destination is a great place to start, as you probably won’t get anywhere if you’re banned from entering the country. You should also check out the local health and safety guidelines of wherever you’re headed so that when you start living like a local, you can keep yourself and those around you safe.

And no matter where you go, having a plan B is always a good idea in case world situations change while you’re off adventuring.

When it comes to more standard vacation fare, you’ll also have a bit to consider there. What to pack, your itinerary, and trip insurance are all worth thinking ahead about — plus, determining based on the length of your stay if you’ll need a visa. You’ll probably also want to have a plan in place for actually getting your work done while you’re away.

How to Ask Your Boss for a Workcation

While each workplace is different, asking your boss for a workcation might be a bit more appealing than taking a chunk of vacation days when your services are needed back at the office.

If you’re already a remote worker and you’re staying fairly local, a quick heads-up might be all you need. However, each company culture is different, so it could vary. Things may get a bit different the farther you stray from home, too. If you’re expecting to work different hours or shift to a different time zone, asking about those details could put you all on the same page.

If other people in your office or workplace have taken workcations before, you may even be able to use their experience as a model — so long as it went well — when you ask your boss about taking some time to work away from your usual spot. Come up with a game plan to stay on top of your tasks and responsibilities to show them you’re still committed to work while you’re away and that you don’t plan to slack off.

If you’re a freelancer, this may not be a problem for you at all. You’re effectively your own boss, so use that to your advantage! Adventure wherever you want to go — as long as you meet your deadlines on time.

Getting Ready for Your Upcoming Workcation

Preparing for working from anywhere is almost the same as preparing for a regular vacation — but with a few extra steps involved.

Since you’ll be working and you can’t totally lounge around on island time all day, you might have a few additional priorities when it comes to what you’re packing, where you’re staying, and what you’ll be doing while you’re there. Packing will obviously involve all the common vacation essentials, but you’ll also want to make sure you have all the technology you need to stay connected. Make sure you have your laptop, charger, and anything else you might need for a regular week of work.

When scoping out locations and accommodations, a high-speed Wi-Fi connection and cell phone service should be high on your priority list. Going off-the-grid seems nice, but not when you have responsibilities to attend to. Ask questions — especially when it comes to more niche stays like Airbnbs or boutique hotels — and make sure you can stay in touch with those who need you.

Making the Most of Your Working Vacation

Are you familiar with the ‘work hard, play harder’ philosophy?

While the “work” part is not to be overlooked, the “vacation” part is still pretty important, too. Prioritizing your activities, having a plan, and creating a balance is key for using your free time effectively. If you have a more flexible schedule, changing up your hours to get in a variety of activities could be a great way to help you feel like you’re truly soaking up all the opportunities of traveling.

And as you shouldn’t put too much pressure on yourself to do everything on your plate, the beauty of a workcation is that you might be able to stretch out your stay a bit longer than you would if you were simply taking time off, so you can do more traveling and relaxing.

Even though you shouldn’t push yourself too much about seeing every sight in your destination, do make an effort to get out and about whenever you can. Unlike back home, where you might spend up to 42% of your waking hours glued to a screen, try to avoid television, smartphone distractions, and internet browsing once work is done.

There’s a world out there, and it’s the reason you’re on this workcation — go and immerse yourself in it. 

How to Be Productive Abroad

How can you make sure your working vacation doesn’t simply turn into a regular holiday?

Just like you need balance to enjoy your workcation to the fullest, balance will also help you maintain the productivity your boss and colleagues are used to expecting from you.

Stick to a routine, and make breaks a regular part of it so you don’t burn out — depending on your work hours, you may even want to try the 20-minute-on, 20-minute-off method for deep work.

Defining your workday by setting standard hours, not overworking yourself, and being clear about managing expectations can ensure you keep your productivity up so you feel satisfied and maintain a sustainable flow.

Taking The Leap

Taking an extended vacation and working from anywhere can be a fulfilling and fun way to change up your workflow, and now is as good a time as ever to set sail.

As long as you stay safe, healthy, responsible, and balanced, you can make your workcation both a relaxing paradise and a productive getaway.


Ginger Abbot is a freelance writer and education enthusiast, as well as the Editor-in-Chief for the education magazine Classrooms.


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