How to Take a Working Vacation in 2021

Right now, you may be thinking about how great it would be to stay at a cabin in the mountains for a few days. You can see yourself and maybe a friend or significant other sitting by a fire while snow fills the backdrop that’s underneath a starry sky. Your days are filled with skiing, and your nights are filled with great conversations around that fire.
Or maybe you’d prefer a secluded cottage by the beach. You go to sleep to the sounds of the ocean like so much white noise, a warm breeze blowing in through the screens, and you get up and enjoy a morning cup of coffee just watching the waves roll in.
While that kind of vacation sounds good, it doesn’t sound possible since you probably have a lot of work to do and barely enough time to get it done.
But have you thought about a working vacation, where you get to go somewhere you’ve wanted to visit, and maybe stay a little longer because you can get your work done.
Now that we’ve been working remotely for nearly a year, the idea of a working vacation doesn’t seem so far-fetched now, does it? In fact, if you had the right work arrangement and followed these steps, you could work in a new city, one week a month, without missing a step.
Here are some tips we’ve figured out working from home down here in South Florida, one of the places people go to on vacation anyway.
First things first, you need to know about the wifi situation in advance. Remember, it’s not a working vacation if you can’t get any work done. So you want to make sure you can get online in the first place. If you arrive at your destination, and it doesn’t have wifi access, that could be a problem.
Ask the property manager or owner about wifi access and speeds. You can also access a site called to see just how fast your Internet service actually is. Also, ask about the strength of the signal and the bandwidth. Traveling to the mountains might be an ideal spot for you, but not if you’re expected to join Zoom meetings or check your emails regularly.
If your destination doesn’t have good wifi, consider getting either a mobile hotspot subscription or unlimited data phone plan so you can connect your phone to your laptop to go online.
Bring the right stuff with you. You need to have the right hardware. Smartphones can do many things, but they are more likely not sufficient for all the work that needs to be done. Consider bringing a laptop or tablet with you before you leave home. You would want to have the right technology to help you do whatever work you need to do. You can work on reports, send emails, and do virtual calls with a device and Wi-Fi connection.
Learn how to go paperless. We’ve written in the past about how you can go completely paperless. This will be important on your working vacation because you don’t want to risk having important files or proprietary information lost or stolen. Keep everything on your laptop, have a backup drive at home or at the office, and keep another backup in a cloud drive like Google Drive or Microsoft OneDrive. And keep important information, like phone numbers and passwords, on a service like Evernote.
Study your local destination. Maybe you don’t want to work at the place where you’re sleeping. Look on Google Maps to see if there are any coffee shops or coworking spaces where you could spend your mornings.
Look at the pictures. Or if you are going to work in your lodgings, see if there are any pictures of the place to make sure you’re going to be comfortable. Will there be a desk and chair for you to work at? Or at least a dining table and comfortable dining chair? Is there enough space between you and your fellow guests, like a private bedroom for you to work while they watch TV? If you’re staying at a hotel, the desk will likely be there, but the space will not. If you’re staying at an Airbnb, well, that’s a crapshoot in finding the best possible setup, but there are plenty of photos for most places.
Don’t focus on work so much. While this is a working vacation, it is a vacation. The whole point of taking a vacation is so you can enjoy your time as much as possible. Vacations are supposed to be full of great moments and a chance to relax. You don’t want to miss those moments because you have to turn in that week’s TPS reports.
So plan for fun and for intentional times with the people you’re traveling with. Let work be the least important aspect of your time away from home.
Have you ever taken a working vacation? Would you? Where would you go and how would you manage it? Share your ideas on our Facebook page, or on our Twitter stream. You can also find us on our Instagram page at @TravelproIntl.
Photo credit: Peggy_marco (Pixabay, Creative Commons 0)