The unprecedented events of 2020 have brought great disruption to people’s livelihoods, with entire sectors facing existential challenges. But at the same time, changes in working arrangements have given many people the opportunity to build a better work–life balance. As office blocks remain closed for the foreseeable future, the growth of remote working has given rise to the ‘workcation’, as many embrace the chance to combine work with travel. But what exactly is a workcation, and how do you take one? We explain all in this guide to workcations, including tips on how to plan one, what to pack, and destination ideas.

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What is a workcation?

Put simply, a workcation is when you take a trip somewhere and combine it with working remotely while you’re there. It’s a chance to clear your head and enjoy a change of scenery while you work, and use your downtime to relax or explore.

Workcations aren’t new – they’ve been around for years. The Wall Street Journal was writing about them five years ago. Until recently this was a niche travel trend, but with so many more people now able to work remotely, it’s becoming more widespread. Not only this, but the growth of virtual learning has also made it easier for families to take workcations together.

Of course, not all jobs are location independent, and so it’s not possible for everybody to take a workcation. If you’re a plumber or a police officer or a factory operative, you can’t exactly do your work from hundreds of miles away. But if your job can be done entirely from a home office, then why not from a sandy beach, a trendy city coffee shop or a comfy hotel suite? Especially if it’s only for a few days, which can give you the perfect headspace to knuckle down on a big project.

Workcations can promote wellness in your professional life and help you find a healthier balance of work and play, among other benefits. Let’s take a closer look…

5 reasons why workcations are a great idea

1.  You don’t use up your vacation or holiday allowance

At Career Gappers, our focus has mainly been on how to take travel career breaks and why time off work is good for you. This hasn’t changed. But at a time when long-term travel has become more challenging, and working life has changed for so many people, workcations offer a great alternative to build more exploration and relaxation into your life without leaving your job or taking a long break.

When taking a workcation, it doesn’t eat into your annual leave for vacations and holidays, because you are doing your job while on the trip. This means you can still take your regular time off work throughout the year to travel, wind down, or however you want to use it.

It’s really important to actually do this; if you take a workcation but then don’t use your regular leave allowance, it defeats the purpose. Treating it as actual time off, when in reality you are working, could be a quick path to burnout. In the USA, in particular, lots of people don’t take their assigned annual leave, and evidence suggests they are missing out on the many benefits of taking a break.

So: take a workcation, but take breaks as well!

2.  Your workflow isn’t disrupted

A workcation provides a way of taking a trip without the disruption to work that a typical vacation can create. That frantic feeling as you scramble to get everything done before setting your out-of-office autoreply? Rushing to brief your colleagues on what needs to be done while you’re away? Coming back to a inbox filled with hundreds of emails that need sorting? You avoid all of that.

Of course, when taking a regular break, you can navigate around these things by planning well. But by mixing some working trips into your calendar too, you can enjoy visiting new destinations now and again without having to worry about those aspects of it.

Lisa workcation San Pedro de Atacama
Working on a hammock, free from distractions… almost

3.  It can boost your productivity

It might seem counterintuitive that working while on vacation would make you more productive. Indeed, paranoid bosses might assume the opposite: “are you really going to get anything done if you’re in a sunny resort by the beach?”

But there are various reasons why a change of scenery can help you to get more work done. Not just while you’re on the trip, but when you get back home as well. Many studies have shown that taking breaks, in particular getting outdoors and among nature, can restore your attention and enhance your productivity.

A change of working environment can give you the headspace to focus on a particular project, away from your regular distractions. Workcations are also a good basis for balancing your time between purposeful working and valuable downtime. Organising tasks into sprints can help you get more done in less time, while recharging in between.

4.  It helps with bigger-picture thinking

One of the major benefits of career breaks is the unique perspective you get by taking a step back. Removal from your daily working environment allows you to assess things from the outside in a way that’s not possible while stuck in your regular routine. The same principle applies to workcations, but on a smaller scale.

A change of scenery gives you a different kind of workspace to focus on big-picture problems and explore new ideas. Meanwhile, unfamiliar surroundings and the opportunity to discover a new place can stimulate your imagination and inspire creative thinking. So, it’s a good idea to take a workcation when you want to focus on strategic planning or creative work.

5.  You feel refreshed you return to work afterwards

Although a workcation is not the same as taking a holiday or vacation, you still get some of the same benefits. Even though you spend time working, the change of environment and opportunity to clear your head can leave you feeling refreshed and recharged after returning home afterwards, almost as though you had taken a complete break.

I have experienced a similar thing when travelling overseas for conferences in the past. Although on those trips I worked more hours than I usually would back home, the combination of seeing a new place and using my off-days to explore left me feeling energised and ready to go again when I returned to the office.

Workcations: busy in Bratislava, Slovakia
Busy at work in Bratislava while the world goes by outside

How to ask your boss for a workcation

This is often the trickiest part. Even if you have the flexibility to work from home in your job, not all managers will be immediately open to the idea of allowing a workcation. You need to be well prepared before approaching your workplace to have the best chance of being granted your request.

Our guide to how to ask for a sabbatical from work covers a lot of the same challenges you will encounter when asking to take a workcation. It’s possible your workplace already has a policy or a precedent for it, but if not, there are few helpful things you can do to prepare.

The crucial thing is to think about what your manager’s biggest concerns are likely to be, and have some solutions ready. They may wonder, what if I can’t contact you easily? How will I know you are getting work done? What happens if everybody else suddenly wants to do this too? All of these concerns can be allayed with a well reasoned case.

At the same time, be ready with positive points about why a workcation would be beneficial to business. The productivity angle is a good one. If you are responsible for a particular project, explain how a different environment will help you focus on it and make progress.

Just as with a sabbatical, timing your workcation can help in having it signed off by your boss. Consider how you can plan it to fit with your organisation’s priorities and work programme. If you can show that you have considered how to bring maximum benefit to the organisation, it will work in your favour.

Finally, give some thought to the logistical arrangements and put forward suggestions on how it will work. Prepare a plan for your work schedule on the trip, what you will be working on, and how people can contact you. Once you have your case ready, write down some notes, rehearse the main points, and raise the question with your boss. It’s a good idea to use a regular meeting if you can, for example if you have weekly one-to-one catchups.

Planning a workcation: the basics

Planning a workcation isn’t quite the same as planning a vacation or holiday. While some aspects are similar, there are a few extra things you need to consider, especially when deciding where to go. These are some of the top considerations:

  • Working space. Think about what your ideal work setup would look like on a workcation and plan accordingly. Would you prefer a hotdesk in a coworking space or hopping between coffee shops? A hotel with working facilities, or a quiet beach where you can work offline?
  • Connection. If your work requires being online, then a location with strong wifi is essential; good mobile coverage likewise if you need to make calls. Check reviews of your accommodation options to see whether you can expect a good connection, or look for somewhere close to a suitable coworking space.
  • Work arrangements. Do you plan to work a full schedule, or could you intersperse some leave days into your trip? When Lisa and I took a recent family workcation to Wales, we split our week fairly evenly between work and time off, which worked out nicely. Also, make sure your lines of contact with your workplace are clear, so they know how to reach you if needed.
  • Timing. When will be the best time for you to take a workcation? The answer to this will be different for everybody. Would you prefer to travel during the off-season or shoulder seasons when it might be quieter? Also, as outlined above, think about the timing that will fit best for your workplace and job responsibilities.

Our guide to travel planning has lots of general tips for designing your trip, and you can read on below for some of our destination ideas for workcations.

JUCY Snooze Hostel in Christchurch New Zealand
Working at JUCY Snooze Hostel near Christchurch International Airport, New Zealand

Tips for getting the most out of workcations

Once your workcation plans are all in place and your flights booked, there’s nothing else to worry about, right? Well, there are still a few things to bear in mind if you want to get the maximum benefit from the experience.

If you haven’t worked remotely before, it may take a little getting used to at first. When I went self-employed and started working from home, it was difficult to find an effective routine and develop good working habits. Our productivity tips for working from home give some insights that are also highly relevant to working remotely.

Establish a routine

Setting a structure for your working days will help to give you focus and divide the lines between work and play. The 90-minute rule is one very effective way of doing this, as described in the productivity tips article linked above. This organises your work into 90-minute sprints, which is optimal for productivity before your brain starts to tune out. Taking breaks in between these shifts will then enable you to recharge.

Whatever structure you use, it’s vital that you do factor in some break time. It doesn’t mean you’re bunking off; taking time out throughout the day will help you to stay fresh and focused when you’re working.

While it’s helpful to have a structure, your routine can still be flexible. If your boss is ok with it, why not mix up your working times while you’re on the trip? For example, on some days you could get up super early and have your work done by midday, allowing you the afternoon to do your own thing.

Switch up your surroundings

The ability to alter your environment is one of the main reasons why workcations can be so effective, so make the most of it, including with your working space if possible.

If you’re using a coworking space that has hotdesks, don’t stick to the same spot for the whole time. If you’re in a town or city, try out different spots, even if it’s having a couple of short sessions in a café during the trip. Mix it up on your breaks and downtime too. Recent studies by universities in New York and Miami have shown that new and diverse experience can make you happier and enhance brain activity.

Try to avoid working where you sleep. I can tell you from personal experience that this will lead to poor sleep, waking up in the middle of the night and first thing in the morning worrying about work. So, don’t set up to work in your hotel room – make sure you have a dedicated working space.

Set boundaries

If you are travelling with other people on your workcation, it will help everyone to have the best possible time if there is a common understanding of your work boundaries. Let others know the times you intend to work, so they can make their own plans accordingly.

On mine and Lisa’s recent workcation in Wales, we travelled with family and stayed together in a holiday cottage. Lisa and I were the only ones working on the trip. By making everyone aware of our working hours, it avoided causing disruption to anyone else’s experience. At the same time, everyone else knew when we would need space for working.

As with anything in life, good communication makes life a lot easier for everyone.

Make it count

If you are taking a workcation for the first time, you have a lot to gain from making a success of it. When your boss sees how effective you can be when working remotely, then they will probably be happy to allow similar arrangements in future.

So, enjoy yourself, make the most of your new surroundings, and hit your work goals – and build a world of possibilities for your future work–life balance.

5 great destinations for workcations

Not everybody’s perfect workcation will look the same, so choosing the right destination is not an exact science. Maybe you will find the ideal headspace for productivity at a private beach resort or off-the-beaten-path village where there are few distractions, or perhaps a funky hostel with working pods in a bohemian city will energise you better. Everybody is different.

While travel restrictions remain in place, try looking closer to home for places where you can get away and work remotely in new surroundings. But for planning future workcations, here are a few destination ideas to help get you started.

1.  Gozo, Malta

Gozo, Malta, is a great destination for off-the-beaten-track workcations
Gozo, Malta, is a great destination for off-the-beaten-track workcations

The second-largest of the three Maltese islands, Gozo fits the bill perfectly for a downbeat getaway for work and leisure. With a population of just 30,000, the island is sparsely populated, with gorgeous natural surroundings. Meanwhile, it is steeped in 7,000 years of history at the heart of the Mediterranean.

In our guide to where to stay in Malta we feature various accommodation recommendations for Gozo. For a luxurious workcation, the five-star Hotel Ta’ Cenc & Spa has private guest rooms in stone bungalows on a complex that includes a business centre with internet access and office supplies. On the southern tip of the island, it overlooks the blue ocean, a world away from your regular office at home.

For a small island nation, Malta offers many alternatives for remote-working trips. Over on the main island, the lively district of St Julian’s is a good option for workcationers seeking a bit more action. This is the epicentre of Malta’s bar and restaurant scene, and also the location of the co-working space Cocohub.

2.  Buenos Aires, Argentina

Palacio Barolo Buenos Aires
In Buenos Aires you can combine a working trip with exploring the ‘Paris of South America’

How about interspersing your work sprints with sipping wine in Argentina’s boisterous capital, or catching a tango show? Buenos Aires is city brimming with energy and culture, and it is also highly equipped for getting some work done. There are working spaces dotted throughout the city, and in particular in the upmarket district of Palermo, which is where many of the city’s best bars and restaurants are (try a steak at La Carnicería, it’s one of the best we’ve ever had!).

Alternatively, there is a vast choice of hotels around the city, as you would expect of a place dubbed the ‘Paris of South America’. We spent a couple of nights at Poetry Building in the Recoleta district, a hotel with an apartment-style feel that had everything we needed to wind down while staying plugged in.

While you’re in the city, there are many ways to use your downtime. Check out our tips on the best things to do in Buenos Aires for ideas.

3.  Bratislava, Slovakia

Old Town Square Bratislava Slovakia
Bratislava’s old town is quieter than many other tourist cities in Central Europe

Central of Europe is bestowed with dozens of ideal cities for taking a working break. Bratislava, at the crossroads of the region, is one that stands out. Its historic old town is full of intrigue, but it is also a quiet and compact city in comparison to others in the region, and lovely to explore over a few days at a slow pace.

Impact HUB is one of a handful of coworking spaces in Bratislava, but none are better located. At the heart of the old town, you could work here a few hours and then walk out into the maze of cobbled roads, gothic architecture, and endless cafés, bars and restaurants. Make sure you try some of the hearty Slovak food while you’re in town.

You could set up a working base in Bratislava through the week and then take trips elsewhere on your days off. Vienna is an hour away down the Danube, while the stunning High Tatra mountains are a few hours’ drive across the country.

4.  Singapore

Singapore Marina Bay Sands skyline
Singapore, one of the world’s most connected cities, has great facilities for workcations

One of the world’s most connected economic centres, Singapore has been ranked the world’s ‘smartest city’ for the last two years, and is rated second only to Tokyo as the world’s safest city. Technology is at the fulcrum of Singapore’s growth, and so the city has much to offer visitors who want to plug in and work during their stay.

Can you imagine working through the day in one of the city’s plush hotels or abundant coworking spaces, and then retiring for a Singapore Sling overlooking Marina Bay Sands? Or if you would rather get under skin of the city’s vibrant multicultural roots, you could explore Chinatown, Little India or grab a budget meal at one of the legendary hawker centres.

We stopped in Singapore for a few days at the beginning of a journey through Southeast Asia; it is the perfect gateway into the region (Singapore Changi has to be the best airport we’ve ever set foot in!). So if you want to tack a little travelling onto the end of your workcation, it’s ideally placed to travel on into Malaysia, Thailand and beyond.

5.  Umbria, Italy

Umbria vineyards valleys
In Umbria you can mix your working days with discovering the region’s wine traditions

Affectionately known as the ‘green heart of Italy’, Umbria is a little bit like Tuscany, but without all the tourists. It is characterised by its rolling valleys, sloping vineyards, hilltop medieval towns, glistening lakes, and friendly, welcoming people. The region ticks all the boxes for a wellness-themed workcation, with its many beautiful hotels, resorts and spas providing a wide choice of relaxing bases.

In Umbria you can mix your working days with getting out into the finest Italian countryside or indulging in some of the best locally produced food and wine you will ever taste. See our guide to the best wineries in Umbria to get an idea of what you can expect. You could even base your Umbria workcation at a wine resort like Altarocca, which looks over the historic citadel of Orvieto, and its rooms and apartments are equipped with free wifi.

What to pack for workcations

Packing for a workcation is a little bit different to packing for a regular holiday or vacation. You don’t just need to think about the clothes and accessories you need for your leisure time, but also the requirements for your working setup. 

With this in mind, these are some of the items to bring that will help you stay productive:

  • Laptop and laptop bag. These are pretty obvious, but you will need them unless you are planning to work completely offline and unplugged.
  • Portable laptop stand. Bringing one of these will help you set up comfortably and keep a good posture.
  • Headset with microphone. Vital if you will be joining any virtual meetings or calls, especially if you will be using a coworking space. 
  • Mouse and keyboard. While it’s fine to just tap away on your laptop, bringing the full complement of desk gear can make your setup more comfortable.
  • Wifi dongle. You can use this as a backup if there is any disruption to your internet connection.
  • Personal planner. Great for setting goals and tracking your progress. It could be fun to use on your outward flight to map out your workcation timeline and objectives.
  • Travel lock. This may come in handy for keeping your valuables secure, particularly if you stay in a hostel or other shared space.
  • Travel insurance. Protect your trip against unforeseen circumstances. We recommend World Nomads, which can be bought from anywhere in the world, and specialises in insuring travellers who work on the road.

Are you planning a workcation or do you have a story to tell about taking one? We would love to help, or even feature you in an interview series we are planning. Please feel free to drop us a line.

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With remote working on the rise, many people are trying out workcations. But what exactly is one, and how do you plan for it? We explain all. #workcations #workcation #remoteworking #takeabreak #wellness

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