Workation Explained: What Is It And How You Can Plan One

Although working from home has become more normalized, it’s not the only option that workers around the world consider. 

In fact, many people are diving into the world of “workations” which allows people to go to a specific destination, work remotely, then log off and get some much-needed rest and relaxation.

This has been a helpful way to increase work happiness, but still have time to enjoy wherever it is someone is working. After all, over 80% of Americans admit to working on vacation or checking in a few hours. 

Below is your guide to all things workation. Including the exact definition, what you need for one, how you plan one, and more. Let’s dive in! 

What is a Workation?

A workation is simply two words combined: working and vacation. And this means you are located anywhere in the world you desire with your normal office hours, but after you finish your work, you then unplug and explore the destination you are visiting. 

Instead of just being in your home office, you now might be at the beach, a completely new city or country, a National Park, etc. The goal is that you are re-energized and productive in this new location, but you can also rest and enjoy sightseeing like you would on vacation. 

The concept of workations is not new, but as remote work exploded in recent years, it gave more people opportunities to change where and when they work.

So does taking a workation mean I’m a digital nomad? 

You might be thinking this sounds like a digital nomad, with which there is some overlap. 

But the difference here is that digital nomads are constantly moving locations for various periods of time. With a workation, you may just go somewhere for two weeks to work and explore, then come back to the home office. 

Workations are typically more popular among those working from home or in the hybrid work model, where the employee combines being in the office and remote. 

How long is a workation?

Most workations should last anywhere from 7 to 14 days, which gives you time to settle, get a bit of a work routine in, and have time for sightseeing and some relaxation. However, you may opt to stay somewhere for a month, but just ensure your employer is okay with that. 

If you work for an awesome remote company, most won’t be concerned with where you work, it’s just ensuring you deliver results. But not every place is onboard with a workation that is longer than two weeks, so be transparent with your manager or HR if you plan an extended one. 

Why do companies send employees on workations?

Although typically a workation is an employee’s idea, sometimes companies also may include this in their work policy or remote work policy as a benefit or perk. The goal of the company is that they hope to increase employee retention, boost productivity, and improve the company culture.

Being in new environments and cultures can also inspire, create new perspectives, and drive creativity. For me, I’m creative in my home office, but I’ve also found working from the beach or a cabin sometimes gives me new energy and focus. 

Now companies who do encourage and offer workations, will also have guidelines. Mostly to ensure employees are still working and not taking advantage of the company’s offer. While there is a vacation component, this is different than just taking personal time off. 

Is A Workation A Good Idea?

A workation can be a good idea, whether you work in the office, hybrid, or remote – as it can be that inspiration you needed to do your best work. Some advantages include making you more relaxed, and creative, giving you new perspectives, and can challenge you to do better work. 

However, a workation isn’t perfect and there can be some downsides. 

The main challenge is that sometimes, you’ll feel it’s hard to disconnect from your work or to disconnect from the vacation aspect. 

Think about this situation, which has probably happened to you before. 

Your normal hours might be done, but then you hear your phone constantly ringing or new Slack notifications popping up. Your fellow colleagues might be in different time zones or not taking a workation. 

It’s why some business leaders argue against workations and it also has its fair share of other critics too. But it’s why if a workation is interesting to you, that some planning is involved and you know where to set clear boundaries. Otherwise, a workation is doing you more harm than good. 

How Do You Plan A Workation?

In order to have a successful workation, you will need to have a plan in place. Sure, you could just get up and go, but you may find yourself disorganized, unprepared, and with an unhappy employer. So here are a few tips to help you plan that workation.

1. Figure out your budget to travel

While it might make sense to pick where you want to go first, I think budgeting should be your main starting point. Otherwise, you may have your heart set on something particular, but realize it’s way out of your workation budget. 

So instead, I’d recommend looking at what you can afford to do currently. This includes any travel costs (airplane ticket, gas, etc.), food, cost of the stay, fun spending money, and anything else. 

2. Pick where you want to go

Once you have a budget planned out, choose where you’d like to go. It really just comes down to asking yourself where would you like to work, but also explore and sightsee. 

Not every workation has to be traveling to a new country or state either. It could be as simple as driving an hour away to a new town and hanging out there for a few days. 

3. Find local amenities and things to do

Once you have your destination picked out, I recommend looking at various amenities or things to do around the town or city. Are there any good coworking spaces, coffee shops, tech stores, sightseeing, or other local events going on while you’ll be there? 

Having various options not only for where you could work, but things you can do will make your workation much more enjoyable. 

4. Plan where you are going to stay

Figuring out where you plan to stay is also key. Do you plan on staying in a hotel, Airbnb, or somewhere else? 

But beyond where you are staying, you need to look for the right things while you are staying there. How’s the internet? Do you have space to set up a small virtual office? Is the place close to essentials and other sightseeing attractions? 

You know the saying: “location, location, location.” 

5. Figure out how long you’d like to stay

Another important item to plan and organize is the length of your stay. You also need to factor in any travel time and get settled in your workation too. 

The last thing you want to do is book something short, but not enough time to get into a nice work and vacation rhythm. 

But it also matters to your employer, your wallet, and if there is a potential need for a remote work visa if you are visiting and staying in a different country for an extended period of time. 

6. When do you plan on going

The timing of your workation is also important to plan. Will it be peak travel season or off-season so you can get better rates and deal with less tourism? Do your homework about wherever it is you plan on going to ensure you don’t have a hectic experience or pay outrageous prices. 

7. Your reasons for wanting a workation

Now, beyond the logistics of your workation, you may still need approval from your employer. And before reaching out to him or her, it’s important to have good reasons for your request. 

Of course, some companies won’t care just as long as the work is done. If that’s your employer, congrats on landing at an awesome place to work! Second, then this planning step won’t really apply to you.

However, if you know you’ll need approval, then write down why you want to have a workation. It can be as simple as feeling burnt out recently and you want to change your scenery to recharge and deliver the best work results possible. 

Think not only about the benefits to you but your employer by being able to go on a workation. 

8. Consult with your manager or HR

There are many companies that offer unique company retreats, flexible work schedules, and other interesting perks. But before you jet off to some new place to start working, the right thing to do is give your manager and company a heads up.

Look, I know there are plenty of remote workers who’ve switched to different timezones or moved states without employers noticing. I just think it’s disingenuous and the right thing to do is a simple heads up and conversation. 

If you get any pushback, you’ll also already have your reasons ready to go from the previous step. If you still get a “no” then it’s something you have to figure out or evaluate your priorities in what you want in a career. And that may mean looking for a new remote job.

What Should I Bring For A Workation?

When you are packing for your workation, you’ll want to make sure you have the essentials to make your experience successful. This will be a combination of the things that ensure you can get work done efficiently, but also enjoy experiences after work. 

Essentials you should consider bringing include:

• Work laptop
• Cell Phone
• Headphones
• Chargers (laptop and phone)
• External hard drive 
• Travel Power Adapters (Pending you go to a different country)
• Extra cables (USB, HDMI, etc.)

Obviously, that’s more work-related items. But you’ll still need your standard travel items like a driver’s license, passport (if going to another country), health insurance cards, credit cards, and cash, etc. 

Where Can You Go On A Workation?

If you are planning a workation, one of the main questions you want to figure out is where you plan on going.

Now if your company is sponsoring this, they may have the whole team head on a workation to a specific place, to boost team collaboration. So at that point, you might not have an exact choice. 

However, generally, you can decide where you’d like to have your workation experience. Many common ones are heading to a beach, or cabin, or getting an Airbnb in a new city or country. 

Here are a few countries you could consider a workation in. These are places that have remote work visas, something you would need if plan on staying longer than a week or two.

• Anguilla
• Bahamas
• Barbados
• Bermuda
• Cayman Islands
• Costa Rica
• Croatia
• Czech Republic
• Estonia
• Iceland
• Germany
• Mexico
• Norway
• Portugal
• Spain

Final Thoughts

According to the Future Forum study, 93% of knowledge workers globally say they want the freedom to decide where and when they do their job. And that’s not surprising! 

Many people experienced the benefits of remote work during the pandemic and realized how much happier and productive they are outside of a cubicle five days a week.  

I do believe over time, we’ll see more organizations encourage and readily approve those interested in taking a workation, even if the employer does not offer full-time remote jobs or even hybrid. At least, those companies who are looking to innovate the workplace and increase employee engagement will. 

Hopefully, this guide was helpful, whether as an individual employee or an employer looking to learn more. Happy workation!

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