Remote work has made it possible to travel without stepping away from your job. Instead of saving up annual leave, many remote workers now combine work and travel by taking a workcation, staying in a new destination while maintaining their normal job responsibilities online.
Compared to a typical holiday, a workcation requires more preparation, which involves factoring in internet reliability, time zone compatibility, and finding the right accommodation before booking anything.
A well-planned work-from-anywhere trip offers more than a typical holiday. It offers the ability to experience a new place at a slower pace without burning through your annual leave. Here’s everything you need to plan your first work-from-anywhere trip.
What does a workcation mean?
A work-from-anywhere trip or workcation means travelling while working remotely. Instead of taking time off, you bring your laptop and maintain your regular job responsibilities online while staying somewhere new.
This could mean spending your mornings completing work tasks and your evenings exploring a new city, trying local food, or visiting cultural attractions. You can plan workcations for a week or two, or you can stay in a destination for several months. This is more common with jobs that allow full location flexibility.
Can I work remotely while travelling abroad on a workcation?
Yes, you can, but there are a few important things you need to consider before planning a workcation abroad.
The first factor is your employer’s remote work policy. While some companies allow employees to work from any location, others require approval to work from another country. It’s also important to consider time zones before travelling for a workcation. If you need to attend meetings at specific hours, travelling to a destination with a similar time zone makes your schedule easier to manage.
Consider visa requirements. While short stays are possible on a tourist visa, some countries now offer digital nomad visas designed specifically for remote workers who want to stay longer. Take time to review these details before travelling, as having all of these in place ensures a smooth work-from-anywhere trip.
How do I plan my first work-from-anywhere trip?
Planning ahead is essential for a successful workcation. Unlike a typical holiday, you will need to consider both travel logistics and your daily work routine. Breaking the process into a few simple steps can make it easier to organise your first work-from-anywhere trip.
How do I get my employer to approve my workcation?
If your role has no location restrictions, then a workcation is the right trip for you. However, ensure your work output and availability remain consistent without affecting your working relationship. On the other hand, if your role has a location restriction or if you are unsure of your remote work policy, then it’s best to inform your manager of your travel plans to avoid any issues.
How do I know which destination is right for my work schedule?
Choosing a destination for a workcation isn’t just about where you would like to visit; it also has to work around your job.
Time zone compatibility is one of the most important factors. If your role involves regular meetings or collaboration with colleagues during set hours, travelling to a location with a large time difference can make your schedule difficult to manage. Destinations within a similar time zone to your home country are usually the safest starting point.
Consider the internet reliability. Without a stable connection, even basic tasks like sending emails or joining video calls can be difficult. Before booking your workcation, check accommodation reviews specifically for mentions of Wi-Fi quality, and research whether your destination has coworking spaces or cafes around as a backup option.
How long should my first workcation be?
As a first work-from-anywhere trip, it’s usually best to start with a shorter trip. A one to two-week trip allows you to test the workcation lifestyle without committing to a long period away from home.
This shorter timeframe helps you see how well you can balance your work responsibilities with exploring a new destination. If the experience goes well, future work-from-anywhere trips can always be longer, and if not, you know where to adjust and plan better.
How do I find accommodation with a good Workspace?
Not every hotel or rental property is suitable for remote work. When searching for accommodation during a workcation, look for places that provide:
- A desk or table suitable for working
- Comfortable seating
- Reliable Wi-Fi
- A quiet environment for meetings
Apartments or short-term rentals are better choices than hotels because they provide more space and flexibility for setting up a temporary workspace. Read guest reviews to help you identify properties where previous travellers have successfully worked remotely.
How do I balance work and exploring during a workcation?
One of the biggest challenges of a workcation is balancing productivity with the desire to explore your destination. Many remote workers find it helpful to create a simple routine. For example, you dedicate mornings to focused work and keep afternoons or evenings free for exploring.
Setting clear work hours helps maintain productivity while still giving you time to enjoy the experience of being in a new environment. Rather than trying to see everything at once, aim for a slower pace that allows you to experience the destination while also accommodating your job responsibilities.
What should I pack for a work-from-anywhere trip?
Packing for a work-from-anywhere trip requires a few additional items beyond normal travel essentials.
Before anything else, pack:
- Your laptop and charger
- Noise-cancelling headphones for calls
- A universal travel adapter
- A wireless mouse or portable laptop stand
- A portable Wi-Fi hotspot, if needed
The right equipment ensures you can work comfortably and stay productive throughout your workcation.
Which destinations are best for a workcation?
The best workcation destination depends on what your job requires, but here are some locations that combine strong infrastructure with an enjoyable lifestyle.
When evaluating any destination, consider four key factors: internet reliability, cost of living, time zone compatibility with your home country, and the availability of coworking spaces or cafés suitable for working.
In Europe, Lisbon and Barcelona remain popular choices thanks to strong connectivity, mild climates, and well-established remote work communities. Cities like Tallinn and Ljubljana are great for remote workers looking for quieter alternatives with a lower cost of living.
In Southeast Asia, Chiang Mai in Thailand and Canggu in Bali can be considered due to their affordable living costs, reliable internet in most central areas, and large communities of digital nomads. Kuala Lumpur is another destination that offers modern infrastructure at a fraction of the cost of many Western cities.
In Latin America, Medellín in Colombia has become one of the most talked-about workcation destinations, combining a comfortable climate, improved infrastructure, and a growing coworking scene. Mexico City is another option worth considering for those based in or travelling from North America, given the manageable time zone overlap.
In Africa, Cape Town stands out for its reliable internet, variety of coworking spaces, and strong English-speaking infrastructure. Nairobi is also a great place to explore for remote workers in East Africa. Work-from-anywhere destinations are not one-size-fits-all. The right destination depends on your budget, your working hours, and the kind of environment where you do your best work.
What mistakes should I avoid on a workcation?
Many people encounter similar challenges during their first workcation.
- Booking accommodation without confirming the quality of the internet connection. Slow or unreliable Wi-Fi can quickly disrupt your workflow.
- Underestimating time zone differences. If meetings take place late at night or early in the morning, it can make the experience exhausting.
- Exploring too much while working full-time. This can lead to trip fatigue. It’s best to create a realistic schedule to help prevent burnout.
By carefully planning and having reasonable expectations, your first work-from-anywhere trip can be both productive and enjoyable.
Conclusion
Working while travelling suits people who are self-directed, adaptable, and comfortable managing their own schedule without the structure of a fixed office. If that sounds like you, a workcation is worth trying.
If you find it difficult to focus in new environments or your role requires significant in-person collaboration, the experience may be more disruptive than rewarding.
The simplest way to find out is to start small. A one or two-week trip tells you quickly whether combining work and travel works for you or not. For many people, even a single workcation is enough to permanently change how they think about work and travel
