The Ultimate Workcation Guide: How to Work & Travel at The Same Time

“Out of Office” has a whole new meaning.

Gone are the days of putting in leave to travel to tropical destinations. With the rise of workcations, you can log on remotely from beach resorts in Cancun, luxury hotels in Greece, and more.

As professionals worldwide are adapting to the fact that their kitchen table is the new office, the hospitality industry is taking notes.

It’s possible to find tailor-made remote work packages giving you everything you need to do your job while soaking up every minute of paradise.

And with more deals springing up, why would you want to put in 8-hours on your couch, when luxury resorts in Negril, Jamaica are calling your name?

Here’s everything you need to know about ditching your kitchen and travelling the world on a workcation!

What is a Workcation?

laptop on the bedroom floor

A workcation is work + a vacation.

It’s a travel niche that has become more popular ever since the pandemic made working from home the new norm.

With long commutes to the office gone, you have the freedom to work from anywhere, so why not swap your couch for something more tropical?

As long as there’s Wi-Fi and a good laptop (click for more information regarding the stores where you could buy these), you can still clock in your hours and disconnect from the humdrum of life while on a beach in Mexico.

Why Now is The Perfect Time to Go on a Workcation

While COVID-19 did give remote work a push, workcations wouldn’t be a thing if it weren’t for technology.

A few years ago, working outside of the office would have been difficult, and a productivity mess, now it’s the opposite.

With lightning-fast internet speeds, video conferencing software, project management software, and virtual team communication, it’s ridiculously easy to get things done without being in the same office.

So why not take advantage and travel while you work?

Why Workactions Are a Good Idea


It’s not only about collecting stamps in your passport, but a workcation comes with a bunch of benefits:

You Don’t Use Your Holiday Allowance

The best part of workcations? You don’t have to dip into your annual leave to explore bucket list destinations.

By making use of an Annual leave planner for staff employees can determine the vacation days they have left for the year for a trip where they do not need to work. This means you can plan effectively to be able to have even more time to travel the world and finally eat a croissant in Paris, hike the Peruvian mountains, or go on safari in South Africa.

It’s almost like you’re getting paid to travel without the brand deals and thousands of followers.

Your Workflow Isn’t Disrupted

Before you go on annual leave, it’s always a stressful experience. You need to scramble to get everything done, hand over projects to colleagues, and remember to set your out-of-office-autoreply.

Then there’s coming back to an inbox of 200+ emails.


With workcations, you don’t need to worry about any of that. All you need to do is buy your flights, pack your bags, and you’re all set to join next week’s marketing meeting from the beach in Bermuda.

It Boosts Your Productivity

I know what you’re thinking.

“How does travelling to new, exciting places BOOST your productivity? How can anyone seriously work while in the Bahamas?”

Well, I’m here to tell you it’s a thing.

Studies have shown that taking breaks, especially getting outdoors, can restore your attention and productivity.

So when you can’t look at your laptop screen for a second longer, taking a dip in the Caribbean Sea can actually make you better at your job.

It’s Healthy for You

Are you someone who struggles to log off?

You’re not alone.

77% of employees struggle to establish boundaries between work and home when the kitchen table is the office.

The solution? A workcation.

With the beautiful beaches of Aruba right outside your door, it’s hard to resist a few hours on the beach. The lure of exploring forces you to take breaks and set up boundaries which create a healthier work environment and bring you back into balance.

How to Plan a Great Workcation


Before you book your flights, here are some things to keep in mind when planning your workcation:

Check Connectivity

Always check out internet access before deciding on a destination.

You need a reliable connection to do your work either at the hotel or a coworking space. It’s also a good idea to look at internet speeds if you need to do regular video calls or send large files.

Plan Your Work Schedule

It’s not a workcation if you spend the whole time working. Before leaving, schedule out your work for the next couple of weeks.

If you can, aim to work between four to six hours per day. It will give you enough free time to socialise, unwind, and explore the destination.

Remember, the more productive and efficient you are with your workload, the more freedom you will have.

Check Visa and COVID Requirements

As with any international travel plans, you’ll want to double-check visa and COVID requirements for U.S. citizens.

Some destinations require a two-week quarantine period on arrival at your expense, while others want to see a negative PCR test.

You may need to show you have enough money for your stay, a return or onward ticket, and at least six months left on your passport.

Book Safe Accommodation

No matter where you go, you want to make sure your accommodation is COVID compliant.

I love that Karisma Hotels has an entire section on their site called “Peace of Mind“. It answers all your questions about COVID, what tests you can expect (yes, they have on-site testing facilities!), and what to expect if you test positive.

Get Travel Insurance

Always buy travel insurance. It’s particularly important when travelling during a pandemic.

If you need to cancel flights or need medical treatment access, you want to make sure you’re covered and not going back home with a massive doctors bill.

Tips for Staying Productive on a Workcation

laptop in a cafe

Worried you might lose focus the minute you catch a glimpse of azure waters? Here are some tips to help you stay productive while working from paradise.

Switch Up Your Desk

Don’t root yourself to one location. Take advantage of your new environment and switch up your work space.

Hotdesk at coworking spaces, go cafe hopping across the city, or swap your hotel room for a spot next to the pool.

Studies show that new and diverse experiences make you happier and enhance your brain activity.

In a nutshell, that means you’ll perform better at your job.

Get into a Routine

When you’re in a new environment, it’s easy to get sidetracked and watch your productivity go down the drain.

How do you stop this from happening on a workcation? A solid routine.

It will give your days structure, help you focus, and divide the line between work and Pina Coladas.

Set Boundaries

Tying into routines are boundaries.

Without them, you’ll find plenty of distractions and a growing amount of work.

Before you arrive for your workcation, time block your calendar. Set aside time for fun activities as soon as you’ve finished work for the day.

It will help you get the best of both worlds, and find balance within your schedule.

Best Workcation Destinations for U.S. Travellers


Need some workcation inspiration? Here are some of the best places to spend your new 9-5.


Only a short flight away from major Northeastern cities in the U.S., Bermuda is the picture-perfect workcation of your dreams!

In between Skype calls and emails, escape to pink-sand beaches, caves with crystal-clear azure waters, and some of the best wreck dives in the world.

If that’s not enough to have you packing your bags, the island nation has a Work From Home Bermuda Certificate. It’s a one year visa which will let you work from the tropical destination for only $263.



Swap the towering skyscrapers of city life for the white sandy beaches of Barbados. The jewel of the Caribbean boasts soft-sand beaches, warm turquoise waters, and spectacular sunsets.

Not only is the island nation affordable, but it comes with high-speed broadband and a remote work visa. Apply for the Barbados Welcome Stamp scheme, and you can work here for up to one year.

Clock out of work and go beach hopping, discover the many historic sites, and ancient Mayan ruins.



Is Mexico’s Yucatan Peninsula on your bucket list? Turn it into your next vacation!

Set up office in the Riveria Maya, and take advantage of the resort workcation packages. Karisma Hotels offers up to 25% rates to working travellers and a slew of other benefits like $1,000 resort credits, 2 for spa packages, and private workspaces.

Use the resort’s prime location to springboard to nearby attractions like Chichen Itza, Holbox Island, and the spellbinding cenotes!



Lying north of Venezuela, Aruba is a gorgeous island getaway. Its stunning coastline attracts sun worshipers from around the world, and its location puts it out of reach from most hurricanes.

When you combine that with its One Happy Workation program (a remote work visa for U.S. visitors), it’s a perfect digital nomad destination.

To get your hands on the visa, all you need is to book a stay with a participating property, and you can take advantage of complimentary WiFi, all-inclusive food and beverages options, and more. However, make sure that you are using their WiFi and it is reliable because this is where most holiday goers end up in trouble, with an unreliable WiFi network. To work this out use a guide like this one on Cell Phone Deal to help you determine safe and secure connectivity.

Dominican Republic


Is summer a bit too far off for your liking? Jet off to the Dominican Republic.

It’s another Caribbean destination with resorts offering enticing remote work packages.

Stay in luxury resorts while exploring the lush forests, mountains, beaches, and semi-desert landscapes. For remote workers who want a workcation that’s more than a beach destination, you can’t go wrong with the Dominican Republic.

Which destination is at the top of your workcation bucket list?