Best Winter Workation and Bleisure Trip Destinations

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  • Post last modified:18/05/2024
Laptop on a yellow sand beach with sunglasses and cocktail.

Hi-de-hi campers, in this post we’re going to explore the origins and meanings of ‘workation’ and ‘bleisure’. Then the best bit, we’ll also tell you about our personal favourite winter workation and bleisure trip destinations based on our own experiences.

Right, let’s cut to the chase and discover more about the two corona-coinages, ‘workation’ and ‘bleisure’

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What is a Workation?

A workation is working away from home for a longer period of time, normally in a different, more desirable, location. It’s a working holiday/ vacation and a close relative of digital nomading. It was made more popular by the restrictions enforced during Covid.

Imagine not sitting in your office every Monday morning. Imagine instead answering the Monday emails from the comfort of the sun lounger on the palm-fringed tropical beach. After a quick dip in the sea and a snack from the lunchtime menu, you might make a start on writing that report.

What is a Bleisure Trip?

A bleisure trip is a cross between a business and a leisure trip. A business trip that includes some free time for sightseeing and enjoying the local culture and customs.  So, you are heading to London for that meeting to close the latest deal. Why join the thongs of people heading back home on Friday afternoon when you can stay until Sunday and swan around Borough Market, take a ride on the London Eye and marvel at the grandeur of Buckenham Palace? After all, the company is paying for it all, right?

A Short History of Workations and Bleisure Trips

Laptop on a yellow sand beach with sunglasses and cocktail.

As a nomadic, remote-working online English teacher, I am more than aware that new words enter our everyday speech all the time. The Rag and Bone Man has been replaced by the recycling centre, the cinema by Netflix, and Marathons by Snickers. Oh [Insert deity of choice], I’m sounding old now. But no single event in recent history has changed our vocabulary more than that dastardly Coronavirus. Suddenly we are barraged by a plethora of new phrases like “flattening the curve”, “social distancing” and, let’s be honest, “Zoom Bar”.

It changed our culture as well. Remote working, distance learning and the hybrid workplace all became a thing. Lockdown forced us all out of the office and into our spare rooms (I wish we had decorated it last year instead of having a holiday on the Isle of Wight). And suddenly Project Manager Johnny realises his boss won’t notice if he works from his spare room or his holiday house on the coast.

And then lockdown (now one word) ends but remote working is still a thing. After all, Johnny’s boss doesn’t have to pay for Johnny’s office space, internet, car parking, electricity etc if Johnny works from home. Desperate to get away for the first time in two years, Johnny uses the money he saved on commuting to work on a three-month holiday in Thailand.

He doesn’t care he only gets five weeks of holiday a year, he’s got lockdown fatigue (aka. cabin fever) and is going whether his boss likes it or not. And now his boss is nervously letting Johnny work from the beach for the remaining time just so he doesn’t have to replace hard-working Johnny.

People have started to take a new outlook on life and realise that there needs to be a balance between work and play. Employers also recognise the importance of reducing fatigue in the workplace. Giving the guys a break now and then pays dividends in the long run by feeding creativity and enthusiasm. Also encouraging people to travel and explore the world only leads to a more understanding and experienced workforce.

The Differences Between Workations and Bleisure Trips

So along with the other corona-coinages (words invented during the COVID era) we now have the words workation (or workcation) and bleisure. They both mean combining work with pleasure. In general, a bleisure trip will comprise a few days working with a little extra time to take in the sights. It is more business and less leisure.

A workation on the other hand is a longer term holiday that includes working remotely on your normal tasks. Bleisure trips used to be only for the director level who were going to important meetings and might include a friendly round of golf and a meal with the customer. Workations used to be limited to digital nomads mainly working freelance in the IT industry or teaching English online. After all, you can code or keyword research from anywhere with an internet connection. COVID changed all of that. It brought these options to the general populous and this is changing the whole tourism industry.

A New Perspective on Destinations for Workations and Bleisure Trips

People are looking at destinations from a whole new perspective. To impress the potential new customer, the next meeting not only needs a swanky meeting place, but it also needs things for them to do for leisure during their downtime. Conversely, the next extended holiday location needs to include great Wi-Fi and an office space to work in. It might have the best bar and beach but it’s useless if you can’t log into the group Teams meeting on a Monday morning.

Winter Workation and Bleisure Trip Destinations

So, the destination is important. And, just as when booking a normal holiday/ vacation, the season dictates the best places to go.

You don’t want a Greek Island beach holiday in January. Trust us, it’s cold and miserable! So, we need to know the best places to go for a workation or bleisure trip depending on what time of year we are going.

Luckily some people are ahead of the curve on this and are already conducting research such as this study of the best winter workations by Holidu. The study lists places that are ideal for either a workation or a bleisure trip.

We were pleased to see we have already explored many of the popular destinations. We recognise that there is a difference in requirements between what makes an ideal winter workation destination and what is great for a winter bleisure trip. We have created two lists. One is our best places for winter workations and the other is our best winter bleisure trip destinations.

Our 5 Best Places for Winter Workations

Yeah okay, we are deeply biased here as we love Southeast Asia. But we have tried to offer a diverse selection of places for your winter workaways. These are in no particular order but just reflect our passion for each place.

If you click on the link for each place you will find out more information and some of the things we got up whilst there.

1. Siem Reap in Cambodia

Image of Angkor Wat and reflection on water.

We worked in Siem Reap for more than two years, Andy teached English online and I freelanced as an SEO consultant. We found the lively tourist town full of excitement and thriving social life. Obviously, you have the Angkor Wat temple complex on the doorstep but the real beauty of Siem Reap and the whole of Cambodia is the people. Both local and expat communities are just a real pleasure to live in. There are enough Western-style provisions there to make life comfortable. The cost of living is amongst the cheapest in the world and the internet is cheap and reliable. I would say it far outweighs that of the UK.

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2. Hoi An in Vietnam

Tanya blogged from Hoi An. It is an amazing town, again with a thriving social scene. The riverside area has some great ancient architecture, along with some great cafes and restaurants. You also have some great beaches on your doorstep. The town retains some authenticity and upholds its chilled-out reputation.

3. Pokhara in Nepal

Colourful wooden boats at the edge of of Pokhara lake with mountains in the background.

I was first in Pokhara in September 2000. It has come a long way from the dirt track streets and genny-powered guest houses. Today it is well on the beaten track and the gateway to the Annapurna range. If you like mountain and lakeside life then this is a great place to live and work. The town is well-equipped and has a more modern feel than some areas of Nepal. The internet is generally fine although it is worth (as always) running a speed test. It also has its own airport so travel to Kathmandu and beyond is fairly quick and easy.

4. Tulum in Mexico

We worked out of Mexico for more than five months and Tulum was one of our favourites. It is laid back and affordable. The great Mexican food and fantastic beaches like Playa Paraiso make it great for easy downtime away from the laptop. There is so much to explain but not enough time, here is a list of words that sum it up. Cenotes, snorkelling, yoga, health food, sharks, food, coral, turtles, palm trees, white sand, hot weather. Just read Tanya’s post about Tulum and then book your tickets.

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5. Barcelona in Spain

View of Barcelona Gothic Quarter

Barcelona is made for workations. It has great work facilities with fast cheap internet and loads of co-working spaces. It has a large and diverse international community and is one of the most popular Spanish cities for expats. It’s large enough for you to find all you need there. The old Gothic Quarter has some amazing buildings including the old cathedral, great bars, and fabulous restaurants. The Raval area has fewer tourists but is more artsy and bohemian. Of course, the beach is full of tourists in the peak season but the winter months are less busy. The only reason it is not at the top of the list is its cost. It is a little expensive in comparison to the other places.

Our 5 Best Places for a Winter Bleisure Trip

Bleisure trips need a little more sway towards the business than the pleasure. You need some quick hits, low-hanging fruit or any other idiom that means easy here to enable you to maximise the potential of your business trip. In other words, you need famous cool stuff close to your hotel so you can quickly nip and see it before you commute back home.

So, the five-day jungle trek to the Lost Temple of Babaganoush with a return journey by white water raft is maybe not an option. But a quick subway ride to the King’s Palace followed by a great authentic local meal is going to be perfectly doable. And in this way, capital cities lend themselves to great bleisure journeys. Plus, large cities have better infrastructure that is less weather-dependent than the more remote locations.

And that’s why all five of our best winter bleisure locations have turned out to be capital cities.

1. Prague in Czechia

Prague, Czech Republic

I first went to Prague for New Year’s Eve in 2005 and instantly fell in love with the place. We have returned many times since and each time find something new to do in the city. Of course, it has all the delights of any European capital city. Check out Charles Bridge, the ancient castle, the old square and the astronomical clock. Mix this with some snow, a glass of gluhwein and the medieval architecture and it becomes a living fairytale. Oh – and it’s not bad as a business centre either.

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2. Istanbul in Turkey

Image of Istanbuls skyline

I would be jealous if you said you had a while to kill in Istanbul before your meeting. The last time Tanya and I were there in 2021, we didn’t want to leave. This two-sided city offers iconic buildings such as the Blue Mosque, The Hagia Sofia, the Grand Bazaar and the huge brand-new Grand Çamlıca Mosque. Add in some of the best food in the world and you have enough to keep you busy for a lifetime, never mind a long weekend in Istanbul. Maybe you could persuade the boss to open a branch office there for you?

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3. Mumbai in India

We started our tour of India on a rainy September day in 2016 in Mumbai. It was hot and humid and we ran around the massive city in a tuk-tuk and taxi taking in the Gateway to India, Marine Drive, and the Coloba Causeway whilst scoffing Pani Puri and 26 different types of curry. Post Colonial Mumbai is not only the Gateway to India, it’s the key to business in Asia.

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4. Bangkok in Thailand

Aerial view of Bangkok city at dusk

Bangkok never gets boring. You could easily kill a year of long weekends there and never be bored with the place. From the magnificent Wat Pho and Grand Palace to the floating market and right down to the street food, this place rocks. My advice is to stay in the business district and avoid the overpriced Khao San Road area. Most hotels here will have a co-working area and great internet.

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5. London in England

Being English, we have to include this steaming cesspit of expensive real estate and thick polluted air. Okay, maybe that’s a bit harsh, in fact, it’s downright unkind and inaccurate. London is home to some of the most iconic buildings in the world. There is plenty to do to keep you busy including The British Museum, the National Gallery, Westminster Abbey, Buckingham Palace, London Bridge, the River Thames, and The London Eye. And that only scratches the surface, it doesn’t even include pie and mash in Bethnal Green! Our favourite area is the East End of London. From a business point of view, it doesn’t get much better than London.

So, there you have it! Before we finish, here is a word of warning. Make sure it is you who wants you to work from a different location and not your slave-driving boss! Make sure you still get that holiday or some downtime away from the laptop, email, work stress and office gossip.

Taking time away from the grindstone to destress, decompress and unwind is more valuable to anyone than any amount of emailing from a sunbed.

If you then feel the urge to go and explore then get out there and enjoy the newfound freedom to travel WITH work.

Planning Your Workation or Bleisure Trip?

Planning your workation or bleisure trip? Here are some of our recommended useful resources to help you have the best time possible.

TRAVEL INSURANCE IS AN IMPORTANT CONSIDERATION! World Nomads offers cover for travellers in over 100 countries and True Traveller is a great option if you’re from the UK or EU.

SafetyWing is another solution, particularly for digital nomads and long-term travellers.

● Find amazing flight deals on Skyscanner,  Kayak, and AirAsia

● Book Asia buses, ferries and taxis with Camboticket or 12Go Asia.  

● For great prices on ferries in Europe check out Ferryhopper.

● Book European trains on Trainline.

● Compare rental car prices on

● Discover fantastic trips and activities with Viator and GetYourGuide.

● Check out Bookmundi, G Adventures, and  Intrepid Travel for group holidays and tours.

Read More Live and Work Abroad

8 Reasons to Use SafetyWing Travel Insurance

Long-Term Travel Insurance – True Traveller and World Nomads

Work From Anywhere With Noad Exchange for Remote Workers

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Andy Korteling

Andy is photographer and content creator for Can Travel Will Travel. He combines online English teaching and freelance YouTube and SEO consultancy with exploring the world. Passionate about sustainable and responsible travel, adventure and food, he incorporates these in his travels as much as possible. He also loves immersing himself in new cultures. He's visited hundreds of destinations in 34 countries and lived in 5 countries. Andy worked as a Project Manager in the Construction and Environmental sectors before leaving the UK in 2016 with his wife Tanya, to travel, live and work abroad indefinitely. Together they share their experiences and useful information to inspire and encourage others to do the same.

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