How to Plan and Pack for a Successful “Workation”

How to Plan and Pack for a Successful “Workation”

By: Rikki Ayers

Working remotely has given me the opportunity to travel to Spain, house sit on an island, and take a week-long cycling trip within the past year. Traveling and working, or “workationing”, poses unique challenges. Will there be good wifi or quiet places to take calls? Is working on your laptop in a café acceptable where you’re going? What if your laptop battery dies while you’re stuck in an airport? Careful planning and packing reduces stress and builds trust with your employer. From choosing the right flights to finding suitable places to stay, this is how you take a successful workation.

Book ahead and schedule buffer days

While spontaneous travel planning is fun and totally acceptable for a real vacation, working while traveling requires planning ahead.

Flight deals are great but when they come with a milk-run itinerary, don’t plan to work while in line or during layovers. Just take the days off.

Book buffer days, a day or two once you’ve arrived with no meetings or deadlines to give you time to get acquainted with your new surroundings, catch up on sleep, and deal with travel issues, such as delayed flights or lost bags.

Avoid traveling around launch days or important meetings. Apply Murphy’s Law to your travel plans: anything that can go wrong will. Don’t jeopardize your job or a client relationship by trying to squeeze an important meeting into a two-hour layover wait because that’s when you’ll find out your next flight takes off from a terminal in another building.

The best times to fly are Thursday nights, Fridays, and Saturdays. Arriving on the weekend gives you time to settle in and explore prior to Monday.

Use flight comparison apps like Momondo, Kayak, Hopper, or Skyscanner to set rate alerts for specific dates. Inform your team of your travel plans ahead of time and when a good deal pops up, you’ll be ready to book without hesitation.

Choose coworking/co-living or business-friendly accommodations    

Staying in hostels is a cheap travel option and a great way to meet fellow travelers, but they’re not always the best places to work from. Do your research ahead of time. Some hostels have quiet work areas, private rooms, and are geared more towards mature travelers, not party animals.

Better yet, find a coworking/co-living situation, such as Nacho Rodriguez’s CoworkingC. These upscale-hostel meets contemporary-office habitats exist specifically for remote workers. Not only is it easier to get work done in a comfortable office setting with good wifi, phone service, and perks like free coffee; they’re also great places to meet other remote workers and participate in workshops and group activities you wouldn’t normally find as a solo traveller. And they’re all over the world. Find them on, Outsite, and CoWoLi.

If sharing space with a bunch of strangers isn’t your thing, then book a business-friendly hotel or an apartment through Airbnb for Work. To be honest, I’ve had better luck with Airbnb, but I typically don’t splurge for hotels. If your company isn’t signed up for Airbnb for Work, you can select “for work” under the trip type filter on the original Airbnb site. These places offer quality wifi, workspaces, and self check-in.    

Scope out work-friendly locations ahead of time

If your accommodations don’t have wifi or you want to spend more time wandering while you work, it’s helpful to find a few trustworthy locations ahead of time. Don’t count on cafés being friendly to remote workers. While staring at laptops in public seems to be gaining acceptance worldwide, in some cultures, especially small towns, treating a café like your office is considered rude and antisocial. Many don’t have wifi.

The Workfrom app can help you find work-friendly spaces close to you. There are also coworking spaces that can be rented on a daily, weekly, or monthly basis. Find those on, Loop, or one of the coworking/co-living sites I mentioned above. Generally, you can also count on Starbucks, libraries, and universities.

Bring the right equipment

Packing for a “workation” is an art. On top of everything you already need for a vacation, like the obvious three pairs of shoes, you also need to fit a laptop and additional gear into your carry-on. I recommend traveling with one bag that can fit in the airplane’s overhead bin. That way, you don’t have to worry about lost luggage.

Depending on how long you’re going for, there are some essentials and nice-to-haves when traveling. Essentials include an international power adapter, headphones with a built-in microphone, and a power bank. A power bank may not seem essential but after running out of battery power on a nine-hour flight and countless times in cafés that didn’t have power outlets, I take my power bank with me everywhere. They’re allowed on most flights (check first) but cannot exceed 100Wh (watt hours).

Nice-to-haves include a portable laptop stand to turn any table or counter into a standing desk, and a Bluetooth keyboard and mouse. These allow you to configure your workspace into something more ergonomic. All that sitting and slouching is terrible for your posture, especially if you’re on an extended trip.  

Traveling while working is a great way to take extended trips, meet fellow remote workers, and gain inspiration from new places and experiences. With careful planning and the right equipment, you can enjoy every minute knowing you’ll be able to meet work obligations without constantly hunting for reliable wifi and a quiet place to focus.

About the Author: Rikki Ayers works remotely as a copywriter and content marketer. She also helps burnt-out office employees rediscover work-life balance through flexible work and lifestyle design via her blog and community, Remote Renegades. Rikki has been writing professionally for over a decade on everything from snowboarding competitions to blockchain technology. And when she’s not working, she’s actively exploring the outdoors. Follow her journey on Instagram at @remoterenegades.