Work from Vacation: The 2021 Trend We All Need

Junction Bridge Little Rock Arkansas
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I’m currently sitting in my cozy hotel room, right in the heart of downtown Little Rock, Arkansas. Amidst all of the rock ‘n’ roll bars, BBQ eateries, and stylish boutiques I am responding to clients, creating marketing plans, and writing email copy. Why? Because 2021 is the year of work from vacation.

If 2020 has taught us anything, it’s that there are no boundaries as to where you can work! 2020 was the year of working from our bedrooms, wearing the same clothes we fell asleep in.

2020 disrupted the work world we were all trying so hard to break down and build new. The pandemic and stay-at-home orders taught us all that we don’t need an office to work in. Even better, it taught us that we don’t even need a corporate job anymore. After the initial lay offs around the world from pandemic lockdowns, more professionals than ever before started freelancing and contracting, deciding it was their time to do what they wanted to do.

What Does Work From Vacation Look Like?

Work from vacation looks like whatever you want it to look like! It can be working with a view of the city’s skyline, from a beach bar in the Caribbean, a cabin in the woods, or from the comfort of your own city’s favorite staycation spot.

2020 helped evolve the remote work world and has brought on new ideas, products, and services to help remote workers find their place in the world.

Read along to find the best countries to work in, the work from vacation essentials, spots to look for, and time management tips.

Best Countries to Work Remotely From

Three words… digital nomad visas. Did you know this was a thing?

A digital nomad visa is offered in many countries throughout the world. The visa allows for remote or freelance workers to stay in the country for an extended period of time while working. Each country has different rules for the digital nomad visa so be sure to check that countries guidelines before visiting.

Some of the top countries with digital nomad visas are: Cayman Islands, Georgia, Iceland, and Ireland. There are plenty more than just the four mentioned here with digital nomad visas.

If the long stay isn’t your thing but you want to get away for a week or two, check out these countries with great remote options.

South Africa

South Africa is a great place to get away for a while but still be connected to great internet speeds. Once you’re there, the cost of living is inexpensive and the country has great day time and night life options – depending on when you choose to work.


Bermuda is a great place to escape for a week. The island is small, the people are friendly, and the sun is warm. The island offers great resorts and hotels – with reliable wifi – to work by the pool then get acquainted with the city at night.


A travelers paradise in South America, what Uruguay lacks in internet speed more than makes up for in adventure and safeness. The country is relatively inexpensive and has plenty of beach resorts to work from.

work from vacation weekend in Little Rock Arkansas
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Remote Working Lounges and Hotels

You read that right.

In the past few years – even before COVID-19 shook up the whole world – places around the globe started catering to the influx of remote workers. Hotels and lounges saw their chance to move into the future and they took it!

Now you can find hotels that specifically cater to the remote worker with quiet spaces, collaboration lounges, and of course, high speed internet from the entire campus.


Outsite is a network of coliving locations around the globe that brings working individuals together in one space to make connections while also getting work done. This program is membership based and once you are a member, doors around the world open up for you.

Not only is this THE network for digital nomads but they focus on building a diverse and sustainable future for for all.

Remote Year

Remote Year focuses on immersing digital nomads into the culture of their host city or country. Don’t let the name scare you off, Remote Year has options for one, four, or 12 month stays.


When your wallet begs you to leave Starbucks, WeWork is the solution. WeWork connects you to co-working spaces around the world for when you’re traveling and need a place to relax and work on your laptop. WeWork has a membership program that opens a variety of locations and office space types for each traveler.

Many cities are introducing their own co-working lounges but WeWork takes away the stress and fuss of finding where to go in each location.

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Work from Vacation Essentials

Work from vacation packing lists can be slightly different than a normal vacations list. On your average vacation, you usually don’t need to worry about wifi and staying on the grid and connected.

While working from vacation, you definitely need to stay connected through your work laptop (obviously), wifi, and your cell phone.

But how can you ensure you are always connected? MiFi’s are one of the greatest inventions for remote workers. Instead of searching for the closest Starbuck’s, you can whip out a MiFi and have internet access wherever there is wireless signal. If you’re going abroad be sure to get a global ready MiFi.

In 2021, this may sound redundant, but pack that extra battery pack. I know phones and laptops have hit a new high of usable battery time, but Zoom’s and FaceTime’s still deplete batteries like cotton candy in water.

Work from Vacation Time Management

I cannot stress this enough – time management matters.

Arriving in a new city is extremely exciting and your sense of adventure and wanderlust may takeover you without warning. This is when you NEED to stick to your plan.

It is super tempting to say ‘I’m on vacation, this project can wait,’ and yes, we’ve all done it before. But remember how stressful is was getting back the day before that project was due and having to complete it all? I do.

Before you leave, beat the procrastination bug in you, and set a schedule.

Use a planner or even put it in your phone or Google calendar so you get alerts. Your designated work time should be focused solely on work. This way the rest of the time is to explore the city.

My own method is waking up early and getting as much done before noon as possible. Once noon hits, the drinks and explorations start!

Whatever your plan is, find one that fits your schedule and needs and stick to it.

Bonus Hits

Join Skillshare Today and Get Two Weeks of Premium for Free!

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Let me know in the comments your favorite work from vacation tips and tricks.

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Follow along on social for more tips, tricks, and travel inspo!

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