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The 6 Do’s and 4 Don’ts of Workcationing in 2020 and Beyond

Daycations, travel pods, and resort bubbles—the tourism industry has certainly leveled up the creativity with this year’s new vocabulary.

As a travel writer, they all piqued my curiosity. So, after months of staying home, I decided to safely wade into the waters of a popular 2020 travel trend: the workcation.

Part regular workday, part vacation, the workcation was inspired by the new legions of people who suddenly found themselves working from their bedrooms and living rooms. From the Maldives to Mexico, hotels around the world began offering special packages to entice these homebound employees to take their work on the road. After all, when you work from home, your “home” can be anywhere there’s WiFi.

For my break from the mundane, I checked into Miami Beach’s Kimpton Surfcomber Hotel to check out its “WFH: Work From Hotel” package, and it was just the escape I needed. If you find yourself planning a workcation, here are some tips to make sure you maximize the experience and avoid any faux pas that may leave your employer thinking of giving you the pink slip.

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Do: Book a Hotel With a Perk-Filled Package

Vacation home rentals are great, but we could all use a few days of pampering while someone else takes care of the details. And if hotels are offering the perks, you might as well take advantage! At the Surfcomber, my WFH stay was complete with complimentary morning coffee, discounts at the onsite restaurant, free printing, and office supplies, plus a complimentary social wine hour to end my workday at 5 p.m. and cheers my way into the evening. When booking your workcation hotel, be sure to compare the different perks that each property offers before making your choice. Don’t forget to look at the regularly-offered amenities as well for a more holistic image of what to expect with your stay.

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Don’t: Be Afraid to Book Something Close to Home

Don’t make the mistake of thinking you have to travel far to enjoy a workcation. Beyond the increased safety of traveling within a driving distance, workcationing close to home also saves you money on transportation, while still giving the novelty of a new experience. Add those dollars to the margarita fund instead. Exploring your area through the eyes of a tourist can also give you a new sense of appreciation for your hometown, as you’re bound to discover new things you had no idea were there before. The Kimpton Surfcomber Hotel is only about 30 minutes from my home, but it felt like a whole new world staying in Miami Beach as a tourist instead of as a reluctant tour guide showing my out-of-state friends around.

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Do: Make Sure There Are Multiple Spots Around the Hotel Where You Could Work From

Sure, you could plan to work from your poolside cabana all day (booking one is definitely worth the splurge), but what happens if it rains? If you move to one of the common areas of the hotel, what happens when a rowdy family decides to join you? Thoroughly check all photos of the property and pay special attention to the areas where you could set up shop for the day, including the guest room itself! Having a Plan A, B, and C will help keep you on track with your work if any issues arise. I encountered a little rain during my workcation at the Surfcomber, but luckily the newly-renovated poolside cabanas were perfectly covered so I didn’t have to retreat inside. The cozy lobby would’ve been my next stop if necessary, though.

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Don’t: Take Work Meetings by the Pool

Reschedule meetings if you must, but whatever you do, don’t take them by the pool. This, of course, depends on the nature of your job and the dynamic among your coworkers, but in general, there’s no need to remind people that you’re catching rays by the pool while they’re at home in sweats. More than anything, taking a meeting by the pool or any other busy common area could be a major distraction and disruption that prolongs the meeting. Don’t be that person. Or, at the very least, keep your camera turned off.

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Do: Bring a Backup Plan for WiFi

While most hotels have fast enough WiFi that you could stream your playlists and have a million tabs open as you work, you’ll occasionally run into a faulty connection. If you can’t afford to lose any time while on the job, be sure to bring a hotspot for backup just in case the WiFi briefly goes down or is consistently weak throughout your stay. The hotspot could also come in handy if the WiFi signal doesn’t reach the pool or other common areas where you’d want to hang out. Keep an eye on the hotel reviews for any mentions of the WiFi as well.

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Don’t: Post on Social Media During Work Hours

It’s tempting to show off your new “office” for the gram, but remember, you’re not totally on vacation and should avoid social media posting while on company time. Do you check your channels and even post while you’re working from home? Probably. But doing so from a hotel may give off a different impression to your boss or coworkers. It may send the signal that you’re not taking your workload seriously because you’re too busy by the beach. It’s not a good look, so keep things on the safe side and post after work. Keep your boss happy enough, and maybe you’ll find yourself workcationing permanently. Hello, digital nomad life.

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Do: Set Expectations With Anyone You May Be Traveling With

Workcationing with friends can make the experience even more enjoyable, but, like a regular vacation, things can also go wrong when expectations aren’t met or misunderstood. I was lucky enough to check out the Kimpton Surfcomber with a friend who was also workcationing, but if you’re traveling with someone who’s on full vacation mode, they may be disappointed by your schedule. Be sure to set boundaries and expectations beforehand so everyone is on the same page about how much time you’ll be able to spend lounging or doing activities together.

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Don’t: Completely Abandon Your Usual Routine

All good things must come to an end eventually, including your workcation. To lessen the blow of returning to regular life, keep up with your routine while at the hotel. Going through your morning or afternoon rituals will also help signal to your brain that it’s time to work even when the crisp hotel sheets are begging you to stay a little while longer. That will set you up for a productive day at work so you can finish on time and get to the fun part of a workcation.

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Do: Finish as Much Work as Possible Ahead of Time

The purpose of a workcation may be to complete your usual work duties in a more idyllic setting, but let’s be real, being surrounded by all those regular vacationers may be distracting and deal a blow to your productivity. To make sure you get everything done with little to no stress, complete as much of your work as possible before checking in. If you can’t manage that, then at least be sure to plan your workdays ahead of time so all you have to do is execute tasks efficiently before enjoying the rest of your day.

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Do: Use Some of Your PTO

One of the best things about a workcation is that it allows you to extend your getaways without using many of those precious—and often too few—vacation days. That said, do yourself a favor and use at least some PTO. Whether it’s to work a few half days or take an entire day off, you deserve some time to be fully present and enjoy the hotel facilities and the surrounding areas.