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Longer vacations are taking off

With widespread flexible work and education schedules, more travelers are turning to flexcations, roadschooling, schoolcations, whatever you want to call them.

Longer vacations are trending.Michael Flippo/

We recently read an article in “The New Yorker” about a family that is traveling the country in an RV, working and roadschooling. The kids log on for their remote learning classes from the back seat or at a campground. In fact, CampSpot, a popular campground reservation company, has mapped out roadschooling routes and suggested learning spots in regions across the country.

Last summer, a friend of ours booked an Airbnb in northern New Hampshire for several months, so he could work remotely and hike the 4,000-footers. Another family we know has booked a private home in Colorado near the Rocky Mountains for the next three months. “Why not?” they say. “We can work, and the kids can study from anywhere.”


It wasn’t that long ago when the big travel trend was the “micro-cation,” a short getaway for people who couldn’t take time off work or afford a big getaway. Travel pundits declared the traditional long, leisurely vacation was a thing of the past.

Well, what a difference a pandemic can make. Today, with widespread flexible work and education schedules, travelers are extending their stays. Flexcation. Staycation. Schoolcation. Roadschooling. Whatever you call it, longer work-play getaways are trending.

“These new days of remote work and a virtual learning environment for children have opened the potential for longer term travel plans for families and young professionals,” says Allison Villasenor, managing director for product, partnerships, and innovation for AAA Exclusive Vacations and AAA Northeast. “Many of our partners, in the Caribbean specifically, are offering longer packages from two weeks to three months, allowing for the work, learn, and stay model. Additionally, quarantine requirements in some locations are making the longer stay a necessity.”

Recent Vrbo travel data supports this new fluidity in vacationing. Key findings in a national study revealed that 50 percent of those surveyed agreed that school schedules are providing more flexibility in vacationing, while 21 percent of respondents said that working from anywhere creates big opportunities for travel during the second half of 2020. Also, interest in one-week or three- and four-week stays has grown, up 25 percent and 15 percent, respectively, compared with the same time last year.


“Since COVID-19 came into our lexicon, we, as a society, have moved through multiple mental phases of this new reality,” says Misty Belles, managing director of global public relations for Virtuoso, a global luxury network of travel agencies with more than 20,000 advisers. “We went from doing whatever to get through the week to the recognition that this new normal is here to stay for a while, and with it comes some opportunities never before realized.

“Work-school-home have converged into the same physical structure, but that place can be located anywhere we choose,” she continued. “That’s actually incredibly freeing, and suddenly the possibility of getting to become semi-permanent residents of another state, even another country, goes from someday to today.”

This change in mindset has led to a jump in demand for villas and private homes, and an increase in extended stays that more closely resemble rental agreements than hotel bookings. And campgrounds are experiencing the same. In a recent survey by The Dyrt, a popular camping trip planning website, 81 percent of parents who responded said they are actively considering remote learning on the road. Kirsten Baughan, a parent in Rhode Island, wrote, “We want to extend our family’s camping season this year and see a great deal of benefit to hitting the road. The kids can do their studies in the mornings and the family can adventure together afterwards! These kids are better off outside.”


CheapCaribbean, a longstanding company specializing in vacation packages to the Caribbean, Mexico, and Central America, is also seeing bookings for stays of 14 nights or more up 12 percent year-over-year, with some resorts reporting the average lengths of stays increasing upward of 30 percent to 50 percent compared to 2019.

“As our data shows, we’ve seen more extended bookings in 2020 than in years prior, likely due to the pandemic and subsequent changes in travel habits of our customers,” says Michael Lowery, senior vice president and general manager of CheapCaribbean,.”Now that remote work has become more prevalent, travelers have the flexibility to commit to longer stays, potentially at lower rates.”

Even high-end, bucket list trips are changing. For example, andBeyond, an award-winning company specializing in custom-made, luxury safaris and tours in Africa, Asia, and South America, is reporting an uptick in longer safaris with fewer stops along the way.

“Where it used to be typical for someone to book a weeklong safari and stop at several lodges, now we’re seeing two- to three-week safaris stopping at only a handful of lodges,” says Nicole Robinson, chief marketing officer of andBeyond. “People are able to take a bit more time now since they can work and do school remotely in a lot of cases, so they’re not in as big of a hurry. Fewer stops also decrease the touchpoints and transfers so guests feel more secure.”


New England vacation properties and resorts are seeing a similar trend. White Elephant Resorts on Nantucket, for example, has seen a 40 percent increase in seven-night stays or more, compared to the 2019 season; some bookings have been six weeks or more. “Normally guests plan multiple trips to multiple destinations,” says Khaled Hashem, managing director of New England Resorts. “Now in the attempt to limit their travel, they are choosing one location for a vacation and extending their time.”

Inn by the Sea in Maine is reporting the same. “Yes, people are staying longer,” says Rauni Kew, PR and green programs manager for the resort. “Recently, we had a family here for 20 days, working remotely and doing home schooling for a change of scene. It made it possible to go to the beach or the pool at recess!”

The industry has responded by dangling unique programs and specials. Montage Hotels & Resorts has launched the Montage Academy, allowing students ages 6 to 17 to enroll in full “school” days, including 24/7 virtual tutoring through, monitored study hall, and educational programing such as yoga, hiking, art, culinary classes, woodshop, conservation, and more. Grand Geneva resort and Timber Ridge Lodge in Lake Geneva, Wis., are offering schoolcation getaway packages, that include monitored schoolrooms for children.

Even international tourist boards are encouraging longer-stay visitors. The Aruba Tourism Authority’s “One Happy Workation” program invites anyone with a valid US passport to relocate to the Caribbean island for 90 days, and a special 12-month Barbados Welcome Stamp visa allows visitors to relocate and work remotely for a year.


Can this possibly be an upside to the pandemic: the opportunity for us to work and for our children to study from anywhere? That’s one glass-half-full way of looking at it.

Diane Bair and Pamela Wright can be reached at