Workation: What it is and How to Plan it

One very positive thing that has come out of the COVID-19 pandemic, is that people have started to reclaim their working lives. Whether that has shown itself through starting their own business, or by leveraging a new WFH schedule.

The same goes for companies. They realized that their employees could still have a productive day while working from somewhere other than the office. In many cases, even better than at the office.

Even though work has become more flexible in many ways, there are still deadlines, meetings, and coworkers. Pressure to perform is still there, as is the need for respite. Enter workations.

What is a Workation?

Unsurprisingly, the word is a combination of work + vacation = workation. Essentially, a workation is defined as a period of time that someone can visit somewhere other than their home, while still being productive in their day job. Similar to a travelpreneur, but with an emphasis on temporary getaways.

Workations give workers the ability to enjoy the benefits of a standard vacation by being in a new, fresh place, but also the added benefit of not having to take time off to do so. For the location-independent workforce that includes remote workers, digital nomads, and WFH employees, this is a huge plus.

What Type of Workation Do You Want?

Typically, the main item that dictates the type of workation you have is time. Other critical factors are cost, number of people, location, but time is the big one. So for your workation planning purposes, let’s break it down by time:

Weekend

Usually this is someplace close to home base. A nearby lake or cabin are popular choices. Air travel isn’t usually part of the equation here, since the time of it would eat into your total workation time.

Week

With a whole week, you have lots of options, whether it’s near you, or on another continent. Booking an Airbnb at your workation destination is an easy way to secure lodging just about anywhere you would choose.

Month

True freedom. If you want to spend the cash, there isn’t anywhere you can’t go with a month long workation. This also makes coliving opportunities a practical option.

Workation for a Weekend

This is certainly the easiest and most practical workation for most people. It’s easy to do if you have kids, or a partner that may not share you’re freedom with work. Additionally, it doesn’t require as much cost as the other two options likely will.

A quick weekend getaway to a beach, cabin, or lake is usually only a couple hours away. Once you pay for food and lodging, there really isn’t much else to pay for if you don’t want to.

Where to Go

Unlike the other time options for workations listed below, a weekend is very dependent on where you’re located. If you’re in New York City, a weekend workation might be to the Catskill Mountains. Remote enough to enjoy nature and get away from the city, but still having wifi.

On the other hand, if you’re in New Mexico, getting away to Colorado Springs might be a good bet. There are plenty of amenities of home, as well as nature, all while not having to deal with Denver traffic.

Regardless, I’ve had the best weekend workations when the locale is between 2-5 hours drive time.

Workation for a Week

With a week or more to use at your disposal, you can likely make any location work as long as it isn’t a long trek to get there. In my opinion, a weeklong workation can give enough time to settle in and enjoy your new surroundings, even while working. It’s enough of an unplug to act as a type of detox, but not so far removed that you dread going back home to your “normal” surroundings.

Where to Go

If you’re based in the United States like me, this could mean that you jet off to a cabin in Canada or a beach in Mexico. If you have 1-3 weeks, then Europe would be a great destination as well.

Everyone is different, but if I’m going to spend more than a day travelling, I want to be able to have more than a week to be at my destination. So for me Europe would be more practical if I had 2 or more weeks.

Workation for a Month…or Longer!

This really is the Holy Grail of workations. The ability to work remotely for a month or more gives you a truly unique opportunity to immerse yourself in your new environment and become a part of it.

When planning a workation for a month or more, the cost starts to play a much bigger part. There are plenty of long-term rentals likely available, but it will be far more expensive than just a week.

Where to Go

When you’re gone for this long, you’ll want to equally weigh the destination with the cost (maybe the cost even more so!). For example, you may have been able to easily pay for a weeklong workation in Paris or London, but a month would be far too expensive. Places like Portugal, Vietnam, or Moldova would likely be much more cost-effective.

Taking into consideration time, cost, and work-friendly environments, here are my top picks for workations that are a month or longer:

  • Portugal
  • Vietnam
  • Costa Rica
  • Colombia
  • Thailand
  • Indonesia
  • Malaysia

These locations all have great remote worker culture, and are very budget-friendly. There are several price breakdowns for these countries online, but generally speaking, you should be able to live easily on $3000 per month in any of these countries. That includes all the main necessities like lodging, food, wifi, utilities, even some entertainment.

I recently went on a 3 week workation to Colombia, and I had a blast. I didn’t feel rushed, finished two website launches, and got to see some amazing sites!

Jared in Colombia on rooftop patio

Common Workation Questions

Can I take a workation with my family?

Absolutely! Obviously you’ll have to take into account their schedule as well, but this is a great option if everyone in the household has that similar freedom. You’ll likely want to choose a location based on where you can stay without breaking the bank, and that still has things that everyone wants to do. If you have kids that will be coming along, you could even find locations that offer camps or classes. Not only would this be beneficial from a learning standpoint, but you would have some distraction-free time to work.

Should I take my employees on a workation?

The short answer is: sure. Who doesn’t like a company-sponsored getaway? The longer answer is: remember what a workation is meant to be. It’s a time that someone has where they can enjoy being able to visit a new/different place, but also work. In some cases, a workation led by the employer may not have the desired effect, as many employees wouldn’t feel relaxed. Keep your team’s expectations in mind before making a decision.

How should I plan my workation?

Generally speaking, you’ll want to plan it mostly like any regular vacation. Most all locations will have reliable wifi, so you’re probably ok there.

That said, to get the most out of your experience, I would suggest making lodging your main criteria over the actual destination. For example, during my recent workation in Colombia, I chose Medellín as the city to visit. The reason I chose there over Bogota or Cali, was for the lodging. The city itself is extremely digital nomad friendly, and Medellín in particular has some amazing hostels that are geared towards getting work done. Almost in the realm of coliving.

Once you figure that out, the rest of the planning really falls into place. The only other suggestion I would make is to be aware of any visa requirements needed if you’re staying longer than 90 days in country. You may subject to different requirements in that case.

Founder : Wherever I May Work | Website | Other Posts

Jared has worked remotely for 15 years in various marketing capacities, and has managed hundreds of marketing campaigns along the way. He has held freelance, agency, and in-house positions for companies large and small.

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