The Ultimate Guide to Planning the Perfect Workation

Posted on January 29, 2021

Have you always dreamed of making a living in paradise? Before you sell off your belongings and escape to a remote beach town for good, consider planning a workcation – also called a workaction or a workation. 

Many employees, freelancers, and small business owners are discovering the magic of relocating temporarily. A workaction makes it possible to enjoy a change of scenery without losing income or using up your vacation days. 

In today's world, technology makes it easy to work from anywhere. All you need is a laptop, a strong internet connection, and permission from your boss. Unless you're self-employed, of course! 

Are you ready to start planning a workaction? We're here to help. Keep reading for the ultimate guide to how to have a workation. 

Because if you have to work, you might as well do it from somewhere warm and beautiful!

What Is a Workaction?

What is a workaction, exactly? It's a working vacation, for times when you need to get away but can't put your job on hold. 

A workcation is a bit of a compromise – you get a break from the office, but not from the daily grind. 

This situation is ideal for individuals such as freelancers and entrepreneurs. They are often tied to their work but have more schedule and location flexibility than traditional employees. 

However, it is becoming more common for all employers to agree to workation requests, as long as the terms are clear. 

Most workactions last about a month, but anywhere from 2 to 6 weeks can work. To maximize productivity, you'll need enough time to settle in and adjust to your new setting. 

Let's look at some of the benefits of taking your job to an exotic locale. 

What Are the Benefits of a Workcation?

There are many reasons why workactions are so popular. Here are some of the benefits you can expect. 


If you're feeling bored, visiting a new place is one of the best ways to seek inspiration. A workation can renew your appreciation for your job. You'll become a more innovative and effective employee.

It's amazing how sipping fresh coconut water can get your creative juices flowing!


Canadian winters are cold. A workaction is an opportunity to thaw out. Also, sunlight is scientifically proven to boost your mood, help you sleep, and reduce the risk of depression.  

Cultural Exchange

Traveling is a great way to meet interesting people, make career connections, and practice your language skills. A workcation can lead to new business opportunities and lifelong friendships. 

Financial Savings

The cost of living is lower in many workaction destinations than in Canada. Choose your work location wisely to save money while you work and play.

Planning a workation requires some thought and organization, but plenty of people manage to do it successfully. Here are our best workaction planning tips.

Recruit Help

Before you commit to a workaction, make sure you have enough help at home. You won't be able to manage every little detail from abroad. 

Delegating basic responsibilities to other team members will leave you with more time to enjoy being where you are. Figure out which tasks can be handled by someone else while you're away. 

If you work independently, hiring a part-time assistant during your workation could be worth the investment. They can help with answering emails, returning phone calls, running errands, and anything else you need. 

At the very least, ask a family member or friend to be your backup. If a business emergency arises that you can't sort out from the beach in Bali, you'll need someone to call. 

Additionally, make arrangements for your pets, plants, and any other dependents. Knowing that they are well cared for will give you peace of mind. 

A lady enjoying her workation on the seaside

Choose Your Destination Wisely

Choosing where to have a workcation is when the fun begins. Exotic, affordable destinations such as Bali, Thailand, and Central America are popular options. You could also visit Spain, Mexico, or the British Virgin Islands. 

There are dozens of workation packages available in India and the Maldives. Or you could reserve an Airbnb a few cities away. 

Before you book your flight and hotel, be sure it's feasible to get work done where you're going. A remote jungle lodge sounds awesome, but how's the WiFi? 

A strong internet connection and cell phone service are essential for productivity and communication. Call your hotel and ask for confirmation that they can provide both. 

You can also check workcation forums and travel review sites to see what other travelers have to say about their experiences. 

Find out if there are coffee shops nearby with free WiFi – you might want to station yourself there for a few hours each day. Does your hotel room have a comfortable desk? Is there a refrigerator for your snacks and bottled water? 

Noise can also be a significant issue when you're trying to concentrate or make phone calls. Try to go somewhere quiet. Avoid notorious party towns, and check the local festival schedule like this one.  Remember, parades, fireworks and parties can be distracting. 

Budget for Your Trip

In many countries, your daily expenses will be lower than at home. In Mexico, for example, dinner from a taco stand might cost less than a cup of coffee in Vancouver. 

But you'll still have to pay your bills in Canada. Invoices for rent and utilities won't disappear because you're out of town. Make sure you know what to expect financially and set yourself up for online bill payment. 

Remember, the goal is always to make more money than you spend! 

Communicate With Your Clients

Not everyone needs to know about your workation plans, but major clients will appreciate a heads up if your schedule is about to change. 

Let them know what to expect. When will you be available to answer calls and emails? Will any projects be put on hold while you're abroad? 

Ask if there's anything you can do in advance to avoid unnecessary complications during your trip. Planning ahead is key to a smooth workcation experience. 

If you're lucky, your clients will recognize your need for a break. They might even give you some extra space until you return. 

Buy Travel Insurance

Smart travelers buy travel insurance. If one thing is for sure, it's that something unexpected could happen on your workaction. 

Lost luggage, delays, and doctor visits are all part of the adventure when you're in a foreign country. It helps to know that you're covered financially if something goes wrong. 

It's unlikely that your regular health insurance will reimburse you for medical expenses incurred abroad. Travel insurance is affordable, so there's no reason to skip it. 

The exact cost depends on your destination, your activities, the coverage you desire, and your insurance history. Choose a reputable company for efficient communication and reimbursement. 

Prepare Your Travel Documents

Is your passport's expiration date approaching? If you answered yes, now is the time to renew it. Some countries won't allow you to enter if your passport is set to expire in the next 6 months. 

You should also check the visa requirements for your destination. If you need a visa, complete the paperwork as soon as possible. Schedule an appointment at the nearest embassy, if necessary. 

Think about banking logistics. You'll need access to cash, so make sure you know your debit card PIN number. 

Let your banks and credit card companies know where you're going so they don't flag your card as stolen when you make a transaction abroad. 

Create a Packing List

If you're heading somewhere warm, you'll need your sandals and sunscreen. But workactions require a few extra items. 

To work efficiently, you'll need the right equipment. To avoid checked bag fees and lugging heavy suitcases halfway around the world, pack smart. 

Bring your lightest laptop, or consider buying a keyboard for your lightweight tablet. Chargers and power cords are essential, as are noise-canceling headphones. You might also need power converters, depending on the electrical outlet configuration where you're going. 

Use your smartphone for calls and photos. You'll want to share your adventures on social media. 

Backup your files on Dropbox or a different cloud storage service so you don't have to carry an external hard drive. Cloud storage can also be useful for sharing files with team members back home. 

If there's a chance the internet connection will be unreliable, bring a portable WiFi hotspot. Research the best options online or contact your cell phone company to find out what solutions they offer. 

Schedule Yourself

Are you heading to a different time zone? Start thinking about when you'll work and when you'll relax. Try to make yourself available for at least a few hours a day when your coworkers can reach you. 

Find the balance between meeting your clients' needs and taking time to explore where you are. You can even sketch out a tentative schedule in your planner.

Having an idea of how you'll spend your time will help you stay motivated. If you wait until you get there to figure it out, you might end up distracted by the excitement of your new surroundings. 

It's also possible to work and vacation at the same time. Answer emails while you sip a mug of coffee at a cafe overlooking the Pacific Ocean,  or grab a seat next to the pool and do business research in your bathing suit. 

There are no rules – the details of your workaction are up to you. 

Most importantly, set reasonable goals. Outline what you want to accomplish while you're away. When you finish, reward yourself with a break or a cultural activity.

After You Arrive

As soon as you arrive at your destination, set up a work station. If there is a desk in your hotel room, place your laptop and chargers there. Create a space where you can mentally transition from vacation to work. 

Take a few days to adjust. Don't be too hard on yourself as you overcome jetlag and find your rhythm. These things take time. 

Try to be flexible and keep an open mind. Even with a solid plan, you will encounter surprises and challenges. Do your best to learn from them. 

Visit a local grocery store and stock your refrigerator with snacks and drinks. You'll be less tempted to wander off to a bar or restaurant if you have what you need within arm's reach. 

Commit to carving out time for yourself. Create a clear division between work and play, and stick to it. You deserve to leave your computer and take in the sights and sounds. 

Avoid answering calls when you're not working, especially if you're in a loud area or you've been drinking. You may be on a workaction, but your clients and coworkers are not. It's important to stay professional. 

Last but not least, eat healthy food and exercise. The last thing you want is to return home feeling like you need a reset. A workcation should be energizing. 

Plan a Real Vacation

While you're on a workcation, allow yourself to daydream about a real vacation. Workcations are great, but you deserve a true break every once in a while.

Even if it's just for a day or two, set an intention to escape in the coming months. Start saving money and head to a place where you can turn off your brain and your technology. 

Make the Most of Your Workcation

Now that you know how to have a workcation, you can start planning your next move. Consult this guide to make sure you follow all the steps for an enjoyable, productive working vacation. 

Whether you fly to Southeast Asia or book a cottage in Banff, you'll gain inspiration and insight and become a better employee, freelancer, or entrepreneur. 

If you do your workcation right, you'll return home happier, healthier, and more inspired than ever before. Who knows, maybe you'll even make it an annual tradition. 

When you're ready to purchase travel insurance, fill out this form to get a quote. You'll love our comprehensive coverage options, supportive customer service, and affordable prices. 

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