[Expert Hours] Join us on March 20th: Maximize Time Off While Ensuring Legal Compliance Register Now

Table Of Contents

The Complete 2023 Guide To Workation

Reading Time: 5 minutes

Table Of Contents

You’re so excited about your upcoming workation or the one you just started planning that you want to skip this intro and go straight to the good stuff – where should I go, and what should I bring?

Don’t worry. We’re not going to be a killjoy. Workation is probably one of the most positive things that came out of the pandemic. We want you to enjoy it and fully take advantage of this experience. 

That’s why we made this 2023 complete guide to workation in which we briefly explain what this term means, give you 3 tips for a successful workation, and name 3 tools that will make your workation go smoother and stress-free. 

What Is Workation? 

Simply put, workation is a combination of work and vacation. Hence, the origin of the term. It implies doing your job in a remote location while enjoying a break from your everyday environment.

The practice of workation has evolved quickly thanks to the pandemic. Today, “only” 3 years after, the US and Europe have a stable trend of taking a workation. Even better. Companies are not only fine with this type of work model, but they organize it for their employees.  

Why’s that? 

It’s simple. Being on workation significantly increases productivity, motivation, creativity flow, and overall work satisfaction. Furthermore, employees who take workations are less likely to experience burnout and leave their jobs for good, even during more intense projects. 

According to the survey conducted with 1000+ Americans at Passport Photo Online, 86% of employees agree or strongly agree a workation boosted their productivity, nearly 69% are less likely to quit after going on workation, 83% agree/strongly agree a workation helped them cope with burnout. In addition, around 84% are now more satisfied with their job.

On the other hand, consequently, companies are earning more money (most likely in less time, too), retaining employees, and advancing their businesses while keeping their employees happy. It’s a win-win situation. That’s why some world-known names, such as Twitter, Facebook, Square, Salesforce, Spotify, Zillow, and Coinbase, allow their employees to work from wherever they want, remote destinations included. 

What Type of Workation Are There? 

There are 3 types of workations depending on their length, and 2 types of workation if we consider the number of people involved. 

Taking into account the length, a workation can be a: 

  • Short-term workation: lasts for a few days, usually in a nearby area.
  • Medium-term workation: from one week to a month, within the country or the continent.
  • Long-term workation: from several months to a couple of years (yes, you read it well!), and for some, it requires work permits according to the laws of the destination country. They are more complicated to organize, as these workations involve moving abroad with all its organizational and legal tasks to handle beforehand. 

Taking into account the number of people involved, a workation can be a: 

  • Solo workation: implies each employee organizing their workation and going by themselves. 
  • Group workation: implies a company organizing a workation for all teams, or some specific teams. 

3 Tips For A Successful Workation

For your workation to go as smoothly as possible, not to affect your work, and for you to use the experience to its maximum, here are 3 things to consider. 

Choose a workation-friendly destination 

First and foremost, be honest with yourself when deciding on the destination of your workation. For example, if you like to party or be entertained after work hours, renting a cottage somewhere in the mountains might not be the best choice for medium or long-term workations. Yes, maybe you want to escape the city for several days, but after a week or two, your experience might turn into frustration. The same goes the other way around. 

Then, speaking about the cottage in the mountains. As much as you want to relax and spend time in nature, you must consider that a stable internet connection is a minimum requirement for you to do your job. Even if you’re not required to jump on meetings every day, there’s a reason why they say – before you move in with someone, let them use the slow internet connection to see who they really are. 

Take into consideration the time difference 

If there’s a time difference between your hometown and the workation destination, take into account the work hours during which you will need to be available. This change may work well for you or make you miss out on many activities your workation destination offers. The latter would mean you just have moved to work and not enjoy the advantages of the new environment, which completely ruins the idea of workation. 

Also, if you don’t take this into account, you might be required to hop on a call or respond to an email after or before the work hours since your team members are still within theirs. As much as this now seems like a message or two, it might now allow you to disconnect from work when on the vacation portion of your experience. 

Remember there’s “work” in workation

Excitement for the new environment can be overwhelming, and you should ensure it doesn’t affect your work hours. Take this experience to learn about yourself, do something different, and try not to make your team doubt what a responsible professional you are. 

Let’s say you stayed up late at night. Then, show up at work on time just like you would if you were in your hometown. If on workation you have roomies while back home, you live by yourself, consider working in a hub or bar instead. If you’re on a group workation sharing an apartment with other colleagues, keep in mind that they are still people with whom you work.

Keep your work and spare time separate like you would back home. 

Top 3 Tools To Help Your Workation Go Smoother 

Any tool to manage remote employees is good to be considered when going on workation. We decided to name the top 3 that significantly help our teams stay on the same page. 

Vacation Tracker 

…or should we rename it for this occasion to Workation Tracker? Jokes aside, Vacation Tracker is a leave management tool that automates the procedures around any time off according to the preset company policies. 

It is suitable even for longer workations that last for a year or longer thanks to the simplicity of customizing its tracking system and adjusting it to comply with different leave laws, public and religious holidays, etc. 

When it comes to short and medium-term vacations, it allows you to request time off in 3 clicks from within your Slack or Teams dashboard. Furthermore, it tracks all types of leaves and keeps you, your team lead, and an HR specialist in the loop by giving instant insight into your complete leave history. 

This is my company logo
Easy PTO tracking, right at your fingertips.

Automate leave policies, improve visibility and plan better

No credit card required. Instant set-up.

Microsoft Teams 

Microsoft Teams is an online, shared workspace ideal for effective communication via direct and group messaging, calls, and video conferencing. As such, it allows team members to catch up briefly on chat or hop on a video call with the possibility of screen sharing for more complex discussions.

As workation is a, let’s say, more enjoyable version of remote work, it is necessary to use a tool that will allow immediate communication despite the spatial gap. Furthermore, Vacation Tracker integrates with Microsoft Teams. You will never have to leave its dashboard to request time off, get notified when approved, check your leave history or the upcoming holidays, and much more. 


Jira is a highly customizable task management platform with detailed project reporting, sprint planning, and task tracking from basic to advanced levels. At any moment, you can see what your work duties for the week or a specific project are, what your teammates are working on, at what stage a task your work may depend, etc., without back-and-forth emailing. 

A task management platform like Jira will help the work part of your workation go smoothly and make you feel like you’re in the office with your team. As far as the organizational side is concerned, that is. It integrates with Microsoft Teams and allows you to manage your tasks within the shared communication workspace. 

To Sum Up  

Being sometimes hard to unplug and get away from job tasks in the remote work models, it seems that new, remote locations bring another level of balance and enthusiasm. 

So, if a workation is here to stay, where are we going next?

Jelena Cerovic
Jelena Cerovic

Jelena turned her love for storytelling and the written word into a full-time job as a B2B content writer and copywriter in the SaaS industry. She reads, dances, and explores new places in her hometown and beyond in her spare time.

Relevance of Hourly PTO for Marketing Agencies

Relevance of Hourly PTO for Marketing Agencies

Read more
Manage Time Off in Lieu (TOIL) in Vacation Tracker

Manage Time Off in Lieu (TOIL) in Vacation Tracker

Read more
TOIL vs. Overtime Pay: What’s Best for Your Business?

TOIL vs. Overtime Pay: What’s Best for Your Business?

Read more

Do you want to simplify PTO tracking?

Schedule a free consultation with our team to learn how Vacation Tracker can help you.

Request a demo