The Ultimate Guide to Taking a Fun (and Productive) Working Vacation

Without your boss finding out!

Working vacation… At first glance, these two words might seem incongruent. Because who wants to work on vacation? But this hybrid approach gives you the best of both worlds: relaxation and productivity, while exploring a new destination.

So go ahead, grab your laptop and boarding pass. Our guide will make sure you’re successful at both parts of this adventure: working and vacationing.

• Choose the right destination

  There’s a sweet spot between the “work” and the “vacation” parts of a working vacation. You want to go somewhere you’ll enjoy, but you have to make sure you can work there.

  Working on a beach sounds great, until you get sand on your keyboard and your phone overheats in the sun. And while the mountains are gorgeous, the WiFi might be spotty—or nonexistent.

  Cities offer WiFi and co-working spaces, plus sightseeing and entertainment. But if you’re not a fan of crowds and skyscrapers, an amenities-laden small town might be just the spot!

• Plan your internet access

  The number one thing you’ll need on a working vacation is good WiFi.

  Staying at an Airbnb? Read the reviews and make sure WiFi issues don’t come up, especially in the most recent reviews.

  And some hotels charge as much as $25 per day for high-speed WiFi! But, you might score free WiFi access if you join their points program.

  Other good solutions: upgrading your cell phone plan to create a WiFi hotspot or working at a library, cafe, or another location with a free, dependable connection.

• Find a good workspace

  Ideally, you’ll be able to find a spot in your hotel room or Airbnb and designate it as your work spot. This will eliminate distractions during business hours, plus make it easier for you to switch into vacation mode at the end of the day.

  If you’re staying with family or friends, though, there may be less space (and more noise). Consider a co-working space to optimize your productivity.

  We’re also big fans of quiet coffee shops with extra-comfy couches!

• Set a schedule

  And stick to it! For your working vacation to, well, work, people need to be able to get a hold of you.

  It’s usually best to keep to your regular schedule, since colleagues, bosses, and clients are already familiar with your availability. That might mean adjusting your schedule, especially if you’re now located in a different time zone.

  If your working hours will be different, reschedule any meetings or calls, update shared calendars, and set up “out of office” messages letting people know when they can expect your reply.

• Remember the essentials

  We know you won’t forget your laptop (and its charging cord, right?), but what else do you need to pack?

  We suggest you spend the week or two before you take off on your working vacation jotting down your “necessities”: noise-canceling headphones, notebook planner, blue-light glasses, your lucky pink pen…

  You know, the little things that help you get through your workday with your sanity intact.

  Pro Tip: Pack professional attire (at least from the waist up) for Zoom meetings and video calls.

• Give yourself plenty of free time

  Maintaining a work-life balance while working remotely can be tough. The same 24/7 access that makes it easy to connect makes it difficult to disconnect!

  Once your office hours are done for the day, turn off your notifications and leave work behind.

  Explore, find new restaurants, meet locals, visit attractions… Get busy enjoying the “vacation” part of your working vacation!

• Leave the right people in the loop

  We know, we know… we said your boss wouldn’t find out.

  But tbh, between your gorgeous social media posts and your Work Bestie, chances are the truth will come out.

  Better to be upfront and let your team know that you’ll be working out of town, but still available and “on” during office hours.

Ready to trade working from home to working from “roam”? Follow our suggestions, and you’ll be able to stay productive while enjoying your vacation time.

And to get a jump start on that relaxation, ship your luggage to your hotel or Airbnb with LugLess. You can breeze through the airport, hands-free, while we make sure that your work gear is waiting for you when you land. Not to mention your favorite vacation stuff… Bermuda shorts and leis, anyone?