Digital NomadTravelTravel Inspiration

Working On Vacation: Here’s What You Need to Know

By 29 April 2024 May 8th, 2025 No Comments

With summer almost here, it’s time to think about mixing work and vacation – something called a workation. Think beaches in Costa Rica, brainstorming amidst the historic charm of Europe, or finding inspiration on a floating retreat, all while getting your work done.

As someone who’s tried working while travelling to be financially free, I get it – it’s a mix of exciting and challenging. But more people are doing it now, and it’s easier than ever with remote work.

So, before you start planning, let’s talk about what workations are, why they’re popular, and how you can make them work for you.

What Is A Workation?

Ever felt torn between needing a break and the pressure to keep up with work? That’s the conundrum many of us face – the desire for vacation battling with the demands of work. But guess what? Workations say you can have both, and they’re gaining popularity for a reason.

The workation trend didn’t just pop up out of thin air. It surged during the pandemic when remote work became the norm. Suddenly, our laptops became our offices, and our options for where to work expanded exponentially.

Think about it: Why be confined to your home office when you could be typing away from a cosy beachside cafe or a charming mountain retreat? With travel restrictions easing up and the world opening back up, the allure of the workation is stronger than ever.

So, if you’ve been yearning for a change of scenery while still crushing your to-do list, it might be time to give the workation lifestyle a try.

How To Plan A Workation

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Before you start the planning process for a workation, notify your employer. You want approval before you depart to avoid violating any policies your remote job may have. Let management know your travel dates, your productivity goals, and if this arrangement will impact your current workflow.

Choose The Right Destination

When planning your workation, it’s crucial to select a destination that offers the right balance between work and pleasure.

Although a rustic lakefront cabin in the woods sounds like a great place to unwind, you may not have the best internet connection to get online while on vacation. Choose a destination that’s not too much off the beaten path.

Along with reliable internet connectivity, consider time zone compatibility with your team or clients. If you’re going on vacation overseas, you may have a hard time connecting if there’s more than a couple of hours of time difference.

You should also consider your work environment. If you’re vacationing with friends and family, you may not have access to a quiet space at your hotel. Instead, you may want to check the availability of co-working spaces.

Manage Your Work Schedule

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Maintaining a productive work schedule is vital to a successful workation. You need a daily and weekly schedule that includes your work times. Build in your free time around your set working hours.

Once you know your availability, communicate your working hours to your team or clients. You should be available by phone, email, and work messaging applications during those periods. Despite being on vacation, you need to demonstrate how reliable you are with getting back to your contacts.

Establish a routine that allows you to dedicate time to work while still enjoying the benefits of being in a new location.

If you’re not using one already, download a productivity app to manage workflow and track assignments. Evernote, Trello, and Monday.com are a few examples of apps you can consider for managing your deadlines.

Travel Insurance And Health Considerations

Remember to take care of your travel insurance and health needs before embarking on your workation. Check if your current medical insurance covers you while travelling. You may need to purchase supplemental insurance to protect you while out of the country.

Research local healthcare facilities and emergency services in your destination. You’ll also want to ensure you’re current on vaccinations before heading to another country.

Stay Connected And Secure

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In order to safeguard your professional reputation, it’s important to ensure that you not only have internet connectivity during your workation but also have the ability to keep any company information secure.

Internet Connectivity

Reliable internet connectivity is essential for digital nomads. Find out what internet access is offered at your hotel or vacation rental.

Depending on the length of your stay, you may need to invest in tools like a portable WiFi hotspot. The hotspot can help you get connected wherever you go.

Another option to consider when travelling is an eSIM. The eSIM is a digital alternative to a physical SIM card that allows you to activate a cellular plan remotely. Devices compatible with eSIMs can accept multiple digital SIM cards at once. Best of all, you won’t rack up roaming charges while on your workation.

If you use public hotspots while working, protect your company information by installing a VPN. A VPN stands for a virtual private network. It encrypts your data to prevent anyone from spying on your device and stealing sensitive information.

It’s also important to understand your travel data requirements, particularly when planning on workation across Europe. With varying eSIM availability depending on the destination and local mobile operators, it’s essential to plan accordingly. This ensures seamless connectivity and efficient communication throughout your travels. 

Data Security

Safeguarding your sensitive data is essential when working remotely.

Alongside employing a VPN, it’s vital to ensure that all your devices are password-protected. If you haven’t updated your passwords recently, it’s advisable to do so before setting off. Never choose an easy-to-guess password. Instead, select a mix of numbers, letters, and special symbols. Enable two-factor authentication when possible. 

Additionally, don’t overlook the importance of keeping your operating systems and applications up to date to patch any potential security vulnerabilities. It’s wise to back up your crucial work files and documents as well. Storage options range from external hard drives to cloud networks.

Cybersecurity Best Practices

When you’re travelling, follow the same cybersecurity practices. Be aware of phishing scams that attempt to have you click on suspicious links or download unknown attachments. Never leave your devices unattended while working away from home. At the end of the day, leave them locked in a safe if one’s available to you.

Be cautious about the information source when accessing emails or websites, especially on unfamiliar networks. Monitor your bank and credit card statements regularly for fraudulent activity. If you see any charges you don’t recognize, your information may have been compromised. 

Monitor your bank and credit card statements regularly for fraudulent activity. If you see any charges you don’t recognize, your information may have been compromised.

How To Avoid Travel Scams

To remain safe while travelling, you need to use common sense and practise extra caution. Trust your instincts and be on alert for any known dangerous areas within your destination.

Research Travel Scams

Research any common travel scams in your destination. The US Department of State is one resource you can check for travel advisories. Common scams include fraudulent tour operators, scam tickets, and pickpocketing. Familiarise yourself to avoid falling victim to scams targeted at tourists.

While travelling, be cautious of your surroundings. If you’re working in a public setting, sit with your back to the wall to avoid displaying your laptop screen.

Seeking Local Advice

When in doubt, seek advice from trusted local travel resources. Tourism offices can provide valuable insights on staying safe online and offline. You could also seek out information from other digital nomads who are working remotely in the same location as you.

Things To Consider Before Going On A Workation

Pros Of Going On A Workation

Change of Scenery

Sitting in the same office day in and day out can feel like Groundhog Day. But imagine swapping that dull routine for the vibrant energy of city life or catching up with work on a wellness retreat.

That’s what a workation offers – a breath of fresh air to reignite your passion for both work and life.

Flexibility

With a workation, you call the shots. Whether you’re an early bird who prefers to tackle tasks at dawn or a night owl who thrives after dark, you have the freedom to design your workday around your natural rhythm.

It’s all about finding that sweet spot where productivity meets personal fulfilment.

Productivity Boost

Ever notice how a change of scenery can spark new ideas and fresh perspectives? That’s the beauty of a workation.

Stepping outside your comfort zone and immersing yourself in a different environment can unleash your creativity and turbocharge your productivity. Suddenly, those nagging tasks feel more manageable, and you’re brimming with innovative solutions.

Travel Opportunities

Who says you can’t have your cake and eat it too? With a workation, you can jet off to exotic locales and explore bucket-list destinations – all while clocking in your 9-to-5.

Picture yourself typing away at a beachside cafe in Bali or brainstorming ideas amidst the hustle and bustle of Tokyo

Networking

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They say it’s not just what you know, but who you know. And what better way to expand your professional network than by mixing business with pleasure?

Whether you’re striking up conversations with fellow digital nomads at a co-working space or rubbing elbows with industry insiders at a local meetup, a workation opens doors to new connections and career opportunities. 

Cons Of Going On A Workation

Work-Life Boundaries

One of the biggest challenges I’ve faced during workations is finding that delicate balance between work and leisure.

When your office is wherever you are, it’s all too easy for work to bleed into your downtime, blurring the lines between professional responsibilities and personal relaxation.

Without clear boundaries, I’ve found myself burning the midnight oil more times than I care to admit, risking burnout in the process.

Slow Internet

Believe me, few things are as exasperating as attempting to meet a deadline while grappling with unreliable Wi-Fi. It’s a perpetual gamble that can leave you feeling as though you’re treading on thin ice with every email dispatched or file uploaded.

In situations like these, having an eSIM can be a game-changer.

In my case, I rely on JetPac eSIM to stay connected wherever I go. With eSIMs, connecting to local carriers for reliable communication and internet access upon arrival becomes effortless. This is especially advantageous for frequent travellers who traverse multiple countries, eliminating the hassle of constantly swapping out SIM cards or relying on costly roaming services.

Time Zone Differences

Working across time zones is like trying to juggle flaming torches – exciting yet incredibly challenging. As someone who’s juggled meetings with clients scattered across the globe, I can attest to the logistical nightmare of coordinating schedules and bridging the gap between time zones.

Hence, you have to position yourself as an expert – it’s all part of the package deal when your coworkers are a world away.

Expense

Let’s not sugarcoat it – workations can put a serious dent in your wallet.

From airfare and accommodation to daily expenses and workspace rentals, the costs can add up faster than you can say “expense report.” And let’s not forget the hidden expenses – like that impromptu networking dinner or the pricey upgrade to faster internet.

It’s a financial tightrope walk that requires careful budgeting and strategic planning to avoid breaking the bank.

Distractions

Whether it’s the lure of sightseeing tours, the allure of local cuisine, or the temptation of impromptu nightlife, distractions abound when you’re working from a new location.

It takes a herculean effort to stay focused and maintain productivity in the face of such enticing diversions.


As vacation and workation season approaches, it’s time to weigh the possibilities and make the most of what lies ahead.

Whether you’re dreaming of stunning beaches or the thrilling cities of Europe, remember that the choice between vacation and workation isn’t always black and white. It’s about finding the balance that works best for you – blending the thrill of exploration with the satisfaction of a job well done.

And in today’s digital age, the opportunities are endless.

Consider leveraging virtual teams to keep your business running smoothly while you’re away, or use the change of scenery as inspiration to revamp your marketing strategies.

Remember, the key to a successful workation is in preparation. By following these essential tips, you can make the most of your workation and ensure a productive and safe experience.

Isabel Leong

Isabel Leong

Full-time travel blogger at Bel Around The World and SEO coach roaming the world at a whim, Isabel helps aspiring content creators and brands get the most out of their online presence by attracting organic leads/traffic and achieving financial freedom with her Skyrocket With SEO course. She's closely involved in and has been featured as a speaker in other travel & digital nomad networks & podcasts such as Traverse, Travel Massive, The Nomadic Network and Location Indie.