Embrace the Flexcation: How to Plan a Working Vacation

Working remotely? After months of video calls and virtual meetings, the notion of working somewhere other than home may sound more appealing than ever. If you’ve been dreaming about temporarily relocating your office to somewhere scenic, know that it’s possible with a flexcation. Also known as a flexible vacation or a workation, a flexcation is when you travel somewhere and work remotely while also taking advantage of your new locale.

Talk to your manager to see if this sort of flexibility is an option for you. Then, use the following tips and insights from real families to make the most of an untethered lifestyle with your loved ones while still logging hours at work. Perhaps you’ll go skiing in Colorado or opt for a food tour of Oahu. The options are endless. When you’re ready, book a flight, rent a car and enjoy your next flexcation destination.

Not sure where to go? Check out The Scenic Route for inspiration.  

Tips for Planning a Flexcation

By booking a rental home with a little extra space, your partner can work in the living room while you and the kids stage a pillow fight in the back bedroom, or vice versa.

Space is important. Although many hotels have updated their offerings to accommodate remote workers, rental homes through companies like Vrbo and Airbnb can offer additional rooms and more space — space that you may want when working in your home away from home. Taking a working vacation is not a foreign concept to Houston residents Aly and Jeff Yale and their 4-year-old twins. If Aly plans to work during one of their trips, they always book a rental home. “With kids, you really have to have some sort of separation in the house if you’re going to be any bit productive,” says Aly, who is a contributing writer for several business and financial publications. “I usually set up shop in a bedroom or somewhere in the back of the house.”

Tip: Before you book your roomy rental, check with the owner to make sure the home is equipped with Wi-Fi throughout the space.

Scheduling is more fun when what you’re scheduling is a family hike.

Be proactive. One of the perks of a flexcation is its flexibility, and upfront planning and scheduling can help you stretch this benefit to the max. For example, know when you want to do family activities in advance. “This lets me schedule my work in and around those outings, so I can be productive and still have fun with the family at the same time,” Aly says.

Also, plan to make mornings and evenings count. Wake up a couple of hours earlier to get a head start on your day’s tasks, freeing up time to do something fun with your family in the afternoon. Likewise, log in before bed to catch up on anything you may have missed and to get organized for the next day.

Have trouble stepping away because you need to keep to a strict work schedule? That’s OK. Keep reading for ways to make your existing work hours work for you.

Take advantage of your scenic surroundings by working next to a window so you can Zoom with a view.

Make the most of a different time zone. Whether you’re traveling with your family or solo, consider traveling outside your time zone but keeping your normal work schedule. This frees up additional hours in the morning or afternoon for exploration. For example, if you work on Eastern time, consider a trip out West to destinations such as Portland, Oregon, or San Diego. Though you’ll be waking up a few hours early to start your day, you’ll have more daylight hours to drive around sightseeing.  

Explore more by taking a few traditional vacation days during your flexcation.

Take a vacation day, or a few. Just because you intend to work while traveling doesn’t mean you can’t (or shouldn’t) take any time off on your flexcation. After discussing with your manager, plan to take a half or full day off, or opt for an extended trip during which you work only part of the week, like Jenny Rogers, who, with husband Chris and their two kids, celebrated the chance to take an extended flexcation to see the kids’ grandparents abroad.

Like many, Jenny and Chris wanted to make up for lost time with their extended family, so they took a four-week trip. Each week, they worked Monday through Wednesday but took off Thursday and Friday. “This meant we could essentially extend our trip while only using eight vacation days. Having the long weekends all month to visit and bond was so wonderful, and then during the days we worked, we had built-in child care with the grandparents,” says Jenny, an instructional designer who lives in Framingham, Massachusetts. “By extending your trip over a few weeks and working part of the week, it means you get more weekends for actual vacation time.”

Tip: It doesn’t hurt to ask your employer for what you want. “If we hadn’t asked, we would never have known we could do it,” Jenny says.

By tag-teaming a flexcation, one partner can focus on work while the other enjoys a little one-on-one time with the kiddos.

Tag-team a working vacation. If both you and your partner are working and you’re not visiting a place with built-in child care, try to stagger your schedules, especially for your meetings. This way one parent can keep an eye on the kids — or even take them to breakfast or a nearby park — while the other concentrates on a call. Later in the day, you and your partner can trade places. “If we know I have a meeting I have to call or Zoom into, we make arrangements for the kids to be out of the house,” Aly says.

Not traveling with kids? Staggering meetings can still be beneficial, especially if you’re not staying in a rental where you and your travel partner can each set up camp in a different room.

Noise-canceling headphones may help you get your job done faster so you can close that laptop and venture out to play.

Pack noise-canceling headphones. Digital nomads suggest packing noise-canceling headphones if you plan to work remotely while traveling. Popping in the earbuds can help you tune out the movie your kids are watching so you can finish what you’re doing and join them sooner rather than later.

Whether you’re planning a flexcation for tomorrow or next year, remember that even though you’re going to work while away, you should make time to vacation some, too. Enjoy yourself, make memories along the way (car games, anyone?) and just have fun.