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Working vacation: pros, cons and how to prepare

Discover how to blend work with leisure effectively on your working vacation. Get the best of both worlds without compromise.


Working vacation

Ever thought about taking your office to the beach or maybe to a cozy mountain cabin? Welcome to the concept of a working vacation, where you can hit two birds with one stone - getting your tasks done while soaking in new experiences around the globe. 

And the good news is that achieving the balance between being productive and experiencing life beyond our desks has become more feasible than ever. Thanks to technology, location flexibility isn’t just a dream anymore; it's very much attainable.

But here's the kicker – planning is key! A successful working vacation doesn't just happen; it requires thoughtful preparation and some savvy strategies

From choosing destinations with reliable internet access to creating boundaries that allow you to truly enjoy your surroundings, there are effective ways to ensure the success of this experience. This guide is here to show you how.

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What is a working vacation?

Picture this: you're sitting on a beautiful beach, sipping a margarita, and soaking up the sun. But instead of fully unplugging, you've got your laptop open and you're cranking out some work. Welcome to the world of working vacations, also known as "workcations".

A working vacation is exactly what it sounds like - a trip where you combine work and leisure. It's a chance to escape the daily grind and experience a new location, all while still getting stuff done. The concept has been around for a while, but it's gained serious traction in recent years as more and more people embrace remote work.

You might spend your mornings working remotely, then hit the beach or explore the local sights in the afternoon. The key is finding a rhythm that allows you to be productive while still enjoying your vacation.

woman working at a cafe during a Working vacation

Pros and cons of taking a working vacation

Before deciding to embark on a working vacation, it's good to weigh the pros and cons to determine if it's the right choice for you.

Benefits of a working vacation

Working vacations provide an extraordinary opportunity to change our working environment and mix up our routines. They not only provide us with the needed break from day-to-day stress, but they can also rejuvenate our productivity and creativity at work. Seeing things from a fresh angle could really amp up your game.

Going on a working vacation also gives you the opportunity to travel to a new place and truly immerse yourself in a new town or country without the need to use up all your precious vacation days. It can encourage great personal growth and the opportunity to experience a place as a local would.

Potential challenges of a working vacation

While the pros of a working vacation are compelling, it's important to consider the potential challenges as well, such as finding the right balance between work and leisure.

It can be tempting to spend more time exploring your new surroundings than focusing on work, and the many distractions can lead to decreased productivity. On the flip side, it's also easy to get caught up in work and neglect to enjoy your vacation.

Logistics might also be an issue. Finding a suitable workspace, reliable internet, and accommodating time zones can be tricky. If you’re traveling solo, you might also worry about feeling alone.

While the cons are valid concerns, they can be mitigated with planning and proactive steps before you head out on your trip.

woman working from a cafe

Planning your ideal working vacation

So, you're sold on the idea of a working vacation. But how do you make it happen? As we’ve mentioned before, planning is key to ensure you have a productive and enjoyable experience. Here are some tips to help you plan a successful workcation:

Choosing your destination

When choosing a destination for your working vacation, consider factors such as time zone differences, cost of living, and the availability of reliable internet access. Look for a location that aligns with your work schedule and offers a balance of work-friendly amenities and leisure activities.

Some popular destinations for working vacations include Bali, Thailand, Costa Rica, and Portugal, which offer a combination of affordable living costs, beautiful landscapes, and vibrant cultures.

Securing reliable internet access

Having a strong internet connection is your best friend for nailing that work-vacay balance. Before booking your accommodation, research the availability and quality of internet services in the area.

Consider staying in accommodations that specifically cater to remote workers, such as co-living spaces or hotels with dedicated workspaces. Many of these options come with the perk of lightning-fast internet and other features to cater for digital nomads and remote workers.

It's always good to have a Plan B. You might consider purchasing a mobile hotspot or international data plan as a backup option and look for coworking spaces in the area.

Selecting suitable accommodations

Besides internet connection, when selecting accommodations for your working vacation it’s important to prioritize comfort, convenience, and a conducive work environment. Look for accommodations that offer a dedicated workspace, comfortable furniture, and ample natural light.

Consider staying in an apartment or vacation rental rather than a traditional hotel room, as this will provide you with more space and amenities to create a comfortable work setup.

make sure your accommodation has a good working space

Striking balance between work and leisure

The key to a successful working vacation is finding the right balance between work and leisure. So, let's dive into a few pointers to help you find that sweet spot.

Creating an effective work schedule

Before embarking on your working vacation, create a realistic work schedule that considers your job responsibilities and the time zone difference between your destination and your home office.

Don't try to cram in a full 8-hour workday if you know you'll be distracted by your surroundings. It's okay to work a bit less than usual on a working vacation.

You might also like to read: 9 tips for staying productive while working from home

Staying productive while enjoying your vacation

Here are a few tips to increase productivity while still making the most of your destination:

  • Determine your most productive hours: Are you a morning person or a night owl? Schedule your work hours around your natural productivity peaks.
  • Before your trip, make a list of your top priorities and deadlines. Focus on these tasks first to ensure you're making progress.
  • Use time-blocking and the Pomodoro Technique to stay focused.
  • Turn off notifications, use website blockers, and find a quiet workspace to minimize distractions.
  • Take regular breaks to avoid burnout and enjoy your surroundings.

Alerting co-workers and clients beforehand

Before departing for your working vacation, inform your co-workers and clients of your plans. Let them know your anticipated work schedule and any potential changes in your availability.

Setting clear expectations upfront will help minimize disruptions and ensure a smooth workflow while you're away.

Designating 'working times' and 'leisure times'

To maintain a healthy work-life balance during your working vacation, designate specific "working times" and "leisure times." During your designated working hours, focus solely on your job responsibilities and minimize distractions.

If you're traveling with family or friends, make sure they understand and respect your work schedule and boundaries.

Outside of your working hours, disconnect from work and fully immerse yourself in your vacation experience. Use tools like Slack's "Do Not Disturb" feature and email autoresponders to protect your off-hours.

make sure you also enjoy your free time during your Working vacation

Making time for leisure activities

Treat your leisure time with the same importance as your work commitments. Block off time on your calendar for beach walks, museum visits, or whatever else brings you joy and fulfillment.

Here are some ideas to help you make that happen:

  • Plan ahead: Research activities and attractions in your destination before you arrive. Make a list of your must-dos and schedule them into your calendar.
  • Take advantage of your surroundings: If you're in a beach destination, schedule in some time for swimming or sunbathing. If you're in a city, plan to visit some local museums or landmarks.
  • Be spontaneous: Don't overplan your leisure time. Leave some room for spontaneity and unexpected adventures.
  • Experience local culture: One of the best parts of a working vacation is the opportunity to experience a new culture. Make sure to immerse yourself in the local way of life, even if you're working part of the time.
  • Try local cuisine: Seek out local restaurants and street food vendors to sample the flavors of your destination.
  • Learn some language basics: Even if you're not fluent, learning a few key phrases in the local language can go a long way in connecting with locals.
  • Attend local events: Check out local festivals, markets, or cultural events happening during your stay.

enjoy local culture by going to street markets and festivals

How to take a working vacation with free accommodation

Want to spend a longer period on the road without paying for accommodation, getting a deep immersion in local culture and meeting interesting people from all over the world, many of which might also be remote workers? A great way to make that happen is by signing up to Worldpackers.

This platform offers an affordable alternative to traditional travel by providing free accommodation in exchange for work. This significantly reduces the cost of lodging, allowing travelers to stretch their budgets further and explore destinations on a slower pace.

Worldpackers hosts a diverse array of work exchange opportunities spanning various industries and locations worldwide. Whether you're interested in hospitality, agriculture, education, community development or other fields, you’ll find something that suits your interests and skills.

Just go to the website, create your free profile, and filter the results by the number of hours of collaboration you can commit to per week, the host type, how you would like to help, travel length, among other criteria.

This is one of the best ways of traveling if you’re eager to live like a local. Unlike traditional tourist experiences, Worldpackers offers travelers the chance to immerse themselves in local communities. By living and working alongside locals, travelers gain deeper insights into the customs, traditions, and way of life of their host country, fostering meaningful cross-cultural connections.

It's also perfect for those traveling alone and seeking community. Through shared experiences, collaborative work, and cultural exchange, you’ll be able to forge connections with like-minded individuals from around the world, creating lasting friendships and networks.

Besides all that, another reason to consider traveling with Worldpackers is safety, which is a concern of many solo travelers. The platform provides support to ensure a positive experience for all parties involved and offers a review system where both hosts and travelers can provide feedback, helping to maintain accountability and transparency within the community.

Since you’re going to be working on your regular job as well, our advice is to look for volunteering opportunities that don’t require too many hours of work. Discuss your work hours and time off with your host before you settle on the work exchange agreement, explaining to them how much time you would need to focus on your own professional endeavors.

Check out a few positions that might be interesting for your working vacation:

Be part of a coliving in the Swiss Alps

Through this opportunity you can get free accommodation in a shared or private room and use all the facilities of this coliving space in exchange for helping facilitate interactions between guests. They look especially for people who have a side job or project and want to learn more about digital nomadism and remote work.

“I had an absolutely wonderful experience at the coliving this winter. Fanny and Haz did an amazing job of briefing Sophia and I, and were there to help with anything we could possibly need. We had a great time getting to know guests, and the work was super easy and flexible, which was great for working and fitting in time for skiing. I'd recommend this experience to anyone, it was once in a lifetime and Grimentz was magical to stay and explore, especially in December”, said former volunteer Olivia, from Australia.

volunteers in the Swiss Alps

Help with website development while you enjoy Costa Rica

This is the perfect opportunity for web developers looking for a working vacation in a paradisiac location. With this host, you’ll get a private room, three meals a day, fast internet access and a dedicated workspace in exchange for 16 hours of work per week.

“My stay with the Ramirez family was really an amazing experience. They have a beautiful home with a warm and welcoming environment. I never felt like I was out of place and every family member tried their best to be helpful and considerate. The location is a great place to spend several weeks. The family care about explaining different aspects of Costa Rican culture which I really enjoyed. I would recommend this experience to Worldpackers who are willing to collaborate and contribute”, said Áine, from Ireland.

volunteer in Costa Rica

Share your music and immerse yourself in Mexican culture

Are you a music fan who wants to share your talent to enrich the lives of others? Then this Guest House in Puebla, Mexico, is the place for you! They are looking for enthusiastic volunteers who have musical skills and are willing to bring the joy of music to people of all ages and backgrounds. They ask for 10 hours of collaboration per week in exchange for accommodation in a private room with fast internet access and a dedicated workspace.

“I had a really good experience at this place. The hosts Luis & Dulce made me feel very welcome and they were super accommodating as well. Even if challenges arose, they were quick to help me fix the problem. This stay felt less about work and more about a true cultural exchange which exceeded my expectations. The other roommates were always kind and respectful. I think Im leaving here with new knowledge about Puebla and new friendships. Thank you guys for everything!”, said former volunteer Telayna, from the USA.

puebla in Mexico

Keep reading: 13 tips for a smooth transition to working remotely

FAQs in relation to working vacation

What is a working vacation?

This allows you to work remotely while also exploring new places and enjoying a change of scenery.

How to plan a working vacation?

Planning a successful working vacation involves a few key steps. First, choose a location that has a reliable internet connection. Next, plan your work hours carefully to ensure productivity. Finally, make sure to carve out time for leisure activities and exploration. Remember, balance is the key to a successful working vacation.

What is an example of a workcation?

An example of a workcation could be taking conference calls from a beach house in Bali or coding from a café in Paris. These scenarios allow you to fulfill your professional duties while also enjoying a unique and exciting environment.

How long should a working vacation be?

The ideal length of a working vacation can vary depending on individual preferences and work requirements. However, a two-week period is often a good starting point. This provides enough time to fully enjoy the chosen location without compromising on professional responsibilities.

Working vacation

As you’ve seen, nailing a working vacation means balancing your time just right - it's all about hitting those deadlines while also creating unforgettable moments.

So as we wrap this up, remember: a working vacation isn’t an escape from responsibilities but rather embracing them in refreshing locales. Enjoy!

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