Work Hard, Play Harder: The Ultimate Guide to Planning a Successful Workation 

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What is a workation? 

With the rise of remote work opportunities, workations are becoming more and more popular. What exactly is a workation? A workation is a combination of work and vacation, essentially bringing your work with you on a trip. 

Workations are a great opportunity to be able to travel for a longer period of time than you would by using your paid time off. 

At the time of writing this, I get 15 paid vacation days per year. That’s not enough for me to take off to the beach for the entire summer.  However, if I were to bring my work with me, rent a condo on the beach for a month, and split my time between working and enjoying the destination during my weekends and free time after work, I can enjoy a longer, extended trip. 

The workation is truly the secret for those who work full-time to be able to enjoy slow travel. 

Advantages of a Workation: 

Aside from being able to travel more and longer, workations have many benefits for your health, well-being, and even your career. 

Improved mental health

Getting away from home and having a change of scenery can do wonders for your mental health and well-being. Choosing a relaxing destination for your workation that will put you at ease and in a peaceful state of mind is the perfect way to unwind, relax, and bring a state of peace and renewed focus to your work. 

Improved productivity

Do you ever find working from home distracting? There’s laundry piling up, dirty dishes in the sink, errands you need to take care of during your lunch break… The endless tasks of daily life can be overwhelming and it’s nice to take a break from those every once and a while. Taking a workation allows you to focus more on your work tasks and leave the daily life tasks behind for a week or two. 

I also find that having something fun to look forward to after work, like a food tour or visiting a museum I’ve been dying to see will motivate me to complete work more quickly (and deter me from procrastinating) so I can go and have fun in the destination I’m visiting. 

Planning a Workation: 

When planning a workation, there are more factors you’ll need to consider compared to planning a typical vacation. The most important of those being ensuring you have a stable internet connection and choosing the right accommodation. 

Internet connectivity: 

First and foremost, you’ll want to have a strong internet connection throughout your workation to be able to complete your work. Having a good internet connection in your accommodation is key. Always ask your hotel, hostel, or Airbnb host for an internet speed test before booking and make sure those speeds are sufficient for your needs. 

Even if your accommodations have great wifi speeds, always have a back-up plan. Research coworking offices in your destination where you can book a desk or office space if needed. 

Having a data plan on your phone with the ability to use it as a hotspot can be a useful tool in a pinch. 

I personally never travel without a backup wifi hotspot, like this one from Travel Wifi. The great thing about this hotspot is, you can purchase packages for almost any destination. The device will connect to the cell phone tower that has the strongest signal in your location. So, as long as there is cell reception where you are, you’ve got internet. 

Choosing your accommodation: 

Hostels: 

As an avid solo traveler, I absolutely love hostels. However, for a workation they are not always an ideal choice. Traditional hostels are typically filled with guests who, understandably, are on vacation. If you’re staying in a shared dorm and the common spaces are all crowded, loud, or don’t have the best wifi you won’t be able to get your work done effectively. 

If you do prefer hostels, look for ones that cater to digital nomads and remote workers. Some things to look for in a hostel: published wifi speeds and co-working spaces. 

Selina is a large chain with hostels all over the Americas, Europe, and even a few locations in the Middle East and Asia. Almost all of their locations have co-working spaces you can use for an additional fee. 

Viajero Hostels have several locations throughout Latin America and many of them feature co-working spaces as well. (I’ve personally stayed and worked from their Miami location and the free co-working space was perfect for my needs.) 

Co-living spaces: 

Another option for your workation, if you prefer a shared and more social environment in your accommodations,  is a co-living space. Similar to hostels, you’ll share a space with other people. However, co-living spaces cater to remote workers and digital nomads specifically. 

They are often large houses with several shared and/or private rooms. Co-working spaces will be set up throughout the house and most rooms are fully equipped with a desk and comfortable workspace. 

As digital nomads and remote workers are typically traveling more slowly and for longer periods of time, many co-living spaces will have a minimum number of days or weeks that you must book to be able to stay. Typically people stay in a co-living space anywhere from a couple weeks to a month. 

I stayed at a co-living space during my workation in Madeira, Portugal, Home Office Madeira, and I absolutely loved it. Being surrounded by other remote workers helped me to stay productive and at the end of the working day, we would explore the island, cook dinner together, or go out for drinks. The experience was similar to having roommates in college. 

How to find co-living spaces in your destination:

Co-living spaces are often not found on the larger, traditional hotel booking platforms. A quick google search of “co-living in {insert your destination” should help you find out if there are any options in the destination you’re traveling to.

Outsite is a company that has several co-living locations around the world.

If you’re looking for someone to take all the workation planning off your hands, consider joining a remote work group trip. Companies like Remote Year and Noma Collective organize 1-month, 3-month, even year-long remote working programs in a variety of different destinations around the world.  

Tips for a Successful Workation: 

With a little planning, taking your remote job with you as you travel can be productive and stress free. Here are some tips for having a successful workcation. 

Don’t try to see too much

When traveling while working, you’ll need to embrace the slow travel mindset. Don’t try to see every major attraction a city has to offer. If you’re out sightseeing before or after work, you don’t want to wear yourself out so much that you’re not able to work productively. 

I try to fit in one short activity per day in my destination when I am working. For instance, when I worked from Lake Bled, Slovenia my working hours were from 3pm – 11pm. I would get up in the morning and go for a short hike, enjoy a late lunch, and then head back to my Airbnb for my work day. 

You could easily fit in a quick visit to a small museum during your lunch break, visit a beautiful park in the morning before your work starts (and fit in a workout!), or join a pub crawl and experience the nightlife in your destination after work. 

Move slowly

One thing I learned after my first workation was to plan to spend at least one full week (including a full weekend) in one location before moving on. (Don’t be like me and make the mistake of moving locations every 3-5 days.) 

You don’t want to be constantly moving and trying to work. You will end up feeling burnt out and exhausted. 

One great strategy for a longer workation is to base yourself in a centrally located city for a couple weeks to a month and take weekend trips from there to other nearby destinations. 

Travel Before or After Work on Less Busy Days

Unless you plan on traveling long distances, like a trans-Atlantic flight or 10 hour bus ride, try to fit in your travel time before or after work. This way you’re not using up your days off on traveling.  

The key to doing this successfully is to choose a day where you are not super busy. (That way you won’t be quite so tired) 

If you’re taking a short train or plane ride of a couple hours or less, it’s easy to fit that travel time in before or after work. 

I like taking an evening flight to my destination, arriving and settling in that night, and I am ready to go and start working from my destination the next day. 

Challenges of a Workation: 

While incredibly fun and rewarding, workations can be challenging. I do enjoy the increased flexibility that working remotely has afforded me to be able to travel more and longer. But I’d be lying if I didn’t share some of its challenges. 

Here are some challenges I have faced with my own workations and how you can overcome those: 

Overcoming feelings of loneliness and isolation: 

Especially if you’re traveling solo, you may feel a little lonely during your workation. I find this can happen, even if I’m staying in a more social accommodation arrangement, like a hostel, if I’m only around other people who are on vacation. If you are the only one working where you’re staying, it may feel a little isolating. 

For this reason, I try to look for hostels or coliving spaces that cater to remote workers and digital nomads. That way I am around other people who are also working and I am bound to meet up with someone who has a similar schedule to me.

Even when I stay in a more private accommodation, such a private Airbnb, I try to fit in a few social activities throughout my week. In my off time from work, I’ll join a group tour or activity. 

Viator, Get Your Guide and Airbnb Experiences are all great places to look for group tours.  Airbnb Experiences are especially helpful for finding nightlife activities. I’ve done mixology classes at a local bar, gone on a locally guided cocktail tour, and done some really fun pub crawls. When you’re working while traveling, these can be a great way to unwind and meet other people after work. 

Organization and productivity: 

Finding a productive space is key to having a successful workation. Think about where you work best at home. Do you prefer working from a public space or your home office? 

If you prefer working from a public space, research co-working spaces in your destination. Many of them may require reservations, so reach out to reserve a desk or office space. If you plan to travel often, a membership to a coworking space, such as WeWork may be beneficial if there are locations in many of the destinations you plan to travel to. 

If you plan on booking a shared accommodation, such as a hostel dorm, you will definitely want to plan to have a quiet and productive workspace, such as a desk in a co-working office. 

I do not recommend relying on coffee shops or cafes as your primary place of work since you’ll be taking up space for several hours while you work, and that is not considerate to the business owners. They need to have that space open for other customers to come in. (And if you’re taking calls or meetings, the other cafe guests may be annoyed as well). 

Getting some quiet work done such as answering emails or writing while you enjoy a coffee is fine, but setting up shop for the entire day after only buying a drink and sandwich is so not cool. Book a desk at a co-working space instead. 

If you do prefer having a private space to work, look for a private room in a hostel or co-living house or rent out an entire home or apartment on Airbnb. Be sure to ask about wifi speed before booking and ask if there will be a designated workspace available as well.  (I’ve made the mistake of booking a hotel room with no desk before and had to get creative to set up a space to take meetings.) 

Keeping a consistent schedule: 

It can be distracting working from a fun destination. While it can be tempting to close your computer and venture out to explore, by staying organized and keeping a consistent schedule you’ll be best able to achieve a manageable work-life balance while on your workation. 

First, figure out what your working hours will be in the destination. Is there a time difference? Do you have set working hours currently or are those flexible? These are all things you’ll need to consider (and maybe discuss with your boss) while planning your workation. 

As I have a customer facing role, I have many meetings scheduled throughout the day and must maintain a consistent schedule based on the time zone where my company is based. So, when I’m traveling I’m working the same work hours and adjust my schedule accordingly based on the time zone of the destination I’m traveling in. Traveling in Latin America is pretty easy for me as it’s in the same time zone as much of the US. When I took a workation in Europe, my work hours shifted to the afternoon and evening. 

If you work on a more asynchronous schedule or make your schedule, plan set working hours in your destination before arriving. This way, you’ll already have a set plan to structure your day. 

Once you know your working hours, make a list of activities or places you can visit outside of that time. For instance, if you’ll be working from 3pm-11pm in Italy, plan to visit a museum you’d love to see in the morning and treat yourself to lunch at a restaurant you want to try before work. If you’re planning a workation by the beach in Mexico and you’ll be working 9am-5pm, plan for a morning run on the beach, a mid-day lunch with a view of the beach, and maybe a sunset surf lesson to end the day. 

If there are a lot of things you want to see or do in a destination, consider taking a longer trip. When you’re working, you can realistically plan to do one small activity per day in your off time. Embrace the fact that you’ll be traveling slower, set yourself a daily routine, and plan to spend a couple weekends in the destination as well (or take a few vacation days). That way you’ll stay on top of your work, and have plenty of time to enjoy the destination during your workation. 

Conclusion: 

If you work remotely, taking a workation is a great way to be able to spend more time in a destination and embrace slow travel. Having a change in scenery and exploring a new destination during your free time is amazing for your mental health as well. With a little planning and preparation, you can be just as productive with work as you are at home.