Why Travelers Are Moving the Home Office Abroad to Work Even More Remotely

It’s mid-October, and Kim and Ian Treibick are racing to wrap up their lives in…

It’s mid-October, and Kim and Ian Treibick are racing to wrap up their lives in the upscale coastal community of Riverside, Conn. The couple have just four days before they move onto their new boat, a Fleming 65, and cast off to cruise south toward the equator for a year, maybe more. “It’s a lifelong dream of mine, to sail off into the sunset, and when we met, we shared that dream,” says Ian, a 43-year-old who works in cryptocurrency. His 39-year-old wife, a stay-at-home mom to three kids aged 10 and under, agrees. “We originally planned to do it after the kids had gone off to college,” she says, pausing. “Then the pandemic hit.” When everyday life upended, they decided to turn the new stay-at-home norms into an adventure by taking a family gap year.

The Treibicks aren’t alone. As the pandemic surges on, more couples and families with the means are following their lead, decamping from the confines of home for longer, or even long-term, trips. With much of life having already moved online in 2020, and further restrictions looming, they reason, why not enjoy isolation somewhere more beneficial, not to mention enjoyable? Families with school-age children, like Kim and Ian, have fewer concerns now about such journeys; kids are familiar with remote schooling already, or parents can simply hire a tutor to travel in a bubble with the family. Those with wanderlust—regardless of whether they have children in tow—are moving abroad for a change of scene, a chance to sate that yen that has been so stymied this year. And travel companies and tourist-starved countries alike have been quick to adapt to the new demand.

The Treibicks have long been travelers, taking regular, albeit shorter, trips. But unmooring from daily routines is possible now like never before—and more appealing, too. Kim and Ian are experienced sailors and persuaded the previous owner of their vessel to sell by telling him about their plans to live, rather than weekend, on board. They’ve sketched an initial itinerary that hugs the East Coast down past Charleston to Palm Beach, while they wait out the end of Caribbean hurricane season. After that, the family will sail west, past the British Virgin Islands to the Blue Hole off Belize for some diving. Costa Rica is a target after that, before sailing through the Panama Canal and over to the Galápagos Islands. “I’m most looking forward to the off-the-beaten-path destinations, like the San Blas Islands in Panama, and going through the canal—that will be a really cool experience,” Kim says.

Before the pandemic, she admits, remote schooling might have given her pause, but the trip feels less intimidating now. Their children have a formal framework for lessons in place via Calvert Academy, an accredited online learning platform, in lieu of their long-term local school. The real learning, though, likely lies beyond a screen. “The kids keep asking about when we’re moving onto the boat, and they’re so excited about the sea life—the dolphins and whales and turtles,” Kim explains. “It’s about seeing different cultures.” Ian will continue to work, remotely. In preparation for their time away he has streamlined his obligations, maintaining existing clients but resisting new business deals. He doesn’t worry about shifting restrictions and red tape from the pandemic, either, as international maritime law requires marinas to allow ships under duress to stop and revictual. Rather, the couple expect their biggest challenge to come next summer, when their initial itinerary concludes. Will they return to life in Connecticut or continue sailing, to the Mediterranean perhaps or west to pinball between the island nations of the Pacific? Ian, for one, is already convinced. “People who do this go for two weeks or until they run out of money,” he says with a laugh. “At this point, I’ll continue until we run out of money.”

Chileno Bay Resort & Residences

Chileno Bay Resort & Residences in Los Cabos, Mexico. Chileno Bay Resort & Residences

Several countries have already recognized the opportunities in luring the bored and affluent to take up temporary residency while the world works from laptops. This past summer, Barbados launched a 12-month digital-nomad visa, the Welcome Stamp, aimed expressly at folks like the Treibicks. The Cayman Islands, Bermuda and Antigua have announced similar programs. In Europe, visitors can live in Estonia via its long-term visa, an extension of its e-Residency program, which was in process before the pandemic, though Americans are still banned under European Union Covid-19 guidelines; Croatia has announced plans to mimic that mechanic and ignore EU precautions, though exact details are still unclear. Thailand goes one better: It offers the visa equivalent of a Centurion Card, called the Elite Card, which bundles perks such as yacht charters and tee times at top golf courses with the right to live long-term in the kingdom. The top tier of this visa costs around $64,000.

Rich Palese, managing partner at charter specialist evoJets, says that only 3 percent of his trip requests in 2019 were for longer than 30 days; from April through September 2020, one in 10 trips were, and 80 percent of those were to non-urban areas. Travel specialists are adjusting their offerings, too. Take Embark Beyond in New York, which in late August created a new division, Embark Longer, that focuses solely on stays of a month or more. Agency founder Jack Ezon tells Robb Report that, in the two months since launch, he has booked 90 trips, all of them structured as leases; the average stay is 2.1 months and the average cost just over $100,000. Brownell Travel, in Birmingham, Ala., has done much the same thing, launching Sojourns by Brownell, a collection of handpicked, five-star properties aimed at stays of a month or more. “Anybody who ever studied abroad had that dream of someday living in Europe or South America, and we learned during the pandemic that time is precious and that the world is your classroom—as long as you have good Wi-Fi,” says Haisley Smith, head of marketing and development. “Long periods sheltering in place made folks dream about it, too.”

It’s easier than ever for Brownell et al. to plan long-term trips, as many top-notch resorts have also adjusted their offerings, specifically catering to those keen to take up temporary residence rather than stay for a long weekend. Consider Remote With Auberge, an umbrella under which the high-end chain is operating two programs, Learn and Work. Learn, for kids staying on the property, features in-person and virtual tutoring services, plus cultural-enrichment classes inspired by each hotel: Think hula dancing and ukulele lessons on the Big Island of Hawaii or classes in Mexican art history in Los Cabos. Adults can book a poolside office cabana or arrange for an in-room office setup, supported by an on-site business concierge, as part of the Work program.

Some travelers, though, prefer to rent a home rather than take up residence in a hotel for their extended stay abroad. Devin Connell, a 39-year-old cooking teacher and blogger, and her investor husband are renting a house in a gated community in Barbados with their two sons, ages five and seven, for at least the first three months of 2021.

Ian Treibick Fleming 65

Ian Treibick at work aboard his Fleming 65. Ian Treibick

The family, from the Rosedale neighborhood of Toronto, has long loved Barbados but usually visited on brief winter breaks, when the Canadian weather was especially bleak. The couple had mulled moving overseas before, but because her husband relied on face-to-face meetings, the options were limited to a global financial center, such as London or Singapore. This year broadened their horizons to include an island in paradise. “My work allows me to be flexible, and now my husband is working remotely. We saw it as a great opportunity for our children to be outside and to detach from the mundane tasks that fill up your day or week,” she tells Robb Report, noting that she has already enrolled her kids in a local private international school so they can meet other children. “There are more opportunities for adventure and to discover things together, immersing ourselves in the local culture. We can take surf lessons at the weekend as a family or discover a cool new part of the island.”

The Eden Roc Cap Cana in the Dominican Republic has reconfigured its luxury villas under its so-called Family Staycations initiative. The hotel has dedicated a children’s concierge to oversee remote schooling: Kids follow distance learning in-suite, and the concierge then chaperones them outdoors for “recess.” Children eat lunch in their family villa, prepped by its private chef, before spending the afternoon taking swimming or Spanish lessons, say, or learning local crafts. Parents are then free to work from “home”—their villa—while the kids are gainfully occupied. Punta Mita’s Four Seasons in Mexico even offers “school-cations” with homework tutors, though not all of its current long-term guests arrived with young children. Erika Baitenmann, 64, is a competitive Paralympic equestrian who typically splits her time between Los Angeles and Mexico City. Considered vulnerable to Covid-19 because of her multiple sclerosis, she has been isolating at the Four Seasons since the spring. The heat has precluded her from bringing her horses to the polo club nearby to continue training, so instead she has been walking and swimming daily. “Short trips are not for me. I need to take my time,” she says by phone from the resort. “I should go back to my regular life in January, but if we have a second outbreak, I will stay on here. There’s no point taking the risk.”

New Yorkers Tana Megalos, 31, and her 38-year-old husband, Jordan Liebowitz, have already committed to their new home. “We’ll probably move here,” she tells Robb Report from the sprawling Acre Baja complex in Los Cabos, where they’ve taken up residence in a villa. “It makes you realize that you don’t need very much. We have one suitcase each and each other.” Megalos works in financial services, while Liebowitz is a real-estate developer. They had celebrated their wedding at this luxury resort in spring 2018 and adopted their dog, Taco, from its pet-rescue sanctuary. The couple have always been drawn to spend an extended stretch in Mexico. Keen travelers, they nonetheless felt unable to do so, at least before the pandemic. “There’s a stigma in the US about taking more than 10 days away,” Megalos notes.

But last June, circumstances shifted. “We were walking Taco in our neighborhood one night and looked up at all the apartments, and they were in complete darkness,” says Liebowitz. “And my office said we were officially going to be remote until August,” adds Megalos, “so that gave us the green light to be anywhere.” The pair rapidly settled on a couple of months in Los Cabos, even though Megalos’s more formalized schedule required her to start work at 7 a.m. local time. But when it was time to come back in August, New York no longer felt like home. They did leave, though, in part to avoid hurricane season and also to pack up their apartment. The couple executed the early-termination rider on their lease and returned to Acre on October 1. They will stay through the end of the year but plan to return to New York in January. “We acknowledge that we’re very, very fortunate to have the ability to do this,” says Megalos. “But the chance to take a step outside the grind and chaos of New York City has been so special.”

Borgo Egnazia

Borgo Egnazia in Italy’s Puglia now offers work amenities, plus a Wi-Fi-free zone. Borgo Egnazia

There are farther-flung options than Mexico or the Caribbean, too: Vakkaru in the Maldives, for example, and its Work Well program, which offers a free upgrade to a larger villa with a study space for any guest booking to stay for 21 days or longer. Borgo Egnazia, a boutique hotel in Italy’s Puglia, now operates a Smart Working program with Soho House–style shared workspace in its common areas, plus conferencing facilities and even a digital-detox area sans Wi-Fi to encourage guests to stop toiling. One country, though, looks likely to be a major long-haul destination for those keen to make their family gap year a bucket-list trip: Kenya.

It’s down to a handy combination of factors, says Deborah Calmeyer, who runs ultra-luxury safari outfit Roar Africa. Some are logistical: Many African countries’ borders remain closed or muddled by red tape, but Kenya reopened early and with a clear testing protocol. An easy, direct flight to Nairobi from JFK on Kenya Airways is a plus, when private airfare might hit $400,000 for the trip. There are other, harder-to-quantify lures, too. “You can go for a game drive every morning, then perhaps exercise before starting school in America in the afternoon,” Calmeyer explains. “Then you do lessons but maybe get called away to see some cheetah cubs that have just been found.” The outdoorsy appeal for parents is evident, as kids swap screen time for nature.

Calmeyer, too, has just launched a new division aimed squarely at those looking to stay in Africa for extended periods, Roar Villas. One of the first to sign up was an American family she had met in the Caribbean and whom she persuaded to move to Kenya for a month; they’re bringing a tutor for their children. “The parents told me they wanted their kids integrated and immersed, out in the wide-open spaces with fresh air and lots of room for them to run around,” she says, then adds with a chuckle, “But, of course, they did ask, ‘What’s the Wi-Fi like?’ just to make sure.” That family will stay at Segera Retreat in Kenya, a villa property that’s effectively on its own compound. This setup is ideal for guests who stay in situ for long stretches and want to wander more freely than they would at most safari camps, which are open to the bush—and the wild animals.

Suzanne Green is another of Calmeyer’s clients. She and her wife, Dana, relocated from their Clark, N.J., home in late 2020 to spend a month at Segera. The couple, 62 and 54, respectively, have visited Africa a number of times but never for such a lengthy period; two weeks was usually the maximum Green could spare from her job as a surgeon. Planned retirement earlier this year, and the turmoil of 2020, propelled the couple to consider a different kind of trip. Family members questioned their traveling so far away right now, but Green is pragmatic. “I feel less safe going to the grocery store, and we’re adventurous with a lot of common sense,” she says with a shrug. “When things here are so damaged, there’s such a pull to reconnect with nature right now, something almost primal. I want to be surrounded by the animals and be far away from what has been my daily routine. Social injustice, the pandemic—both stresses have taken a toll on us.” Green hopes that this vacation will be just the first of several extended African stays for the couple in the near future.

Acre Baja

New Yorkers Tana Megalos and Jordan Liebowitz, with their dog, Taco, at Acre Baja in San José del Cabo, Mexico. Acre Baja

The shift toward longer live/work trips among well-heeled travelers like Green, the Treibicks and Connell has been dramatic. And don’t expect that newfangled wanderlust to dwindle anytime soon, says Calmeyer. “If I’d suggested to my clients at the same time last year, ‘Why not come for a month?,’ they’d have laughed,” she muses. “Everyone wants to do it now.”

Things to Know Before You Go

For anyone considering taking an extended trip like these, Brownell Travel’s Haisley Smith suggests asking the following questions to help determine the best destination and type of trip. Call them the seven C’s:

Communication: Is an English-speaking destination important, or are you looking for a language immersion?

Cooking: How do you prefer to eat? Love to cook and need a grocery store nearby? Would you rather eat every meal at a restaurant? Or is a private chef essential?

Connections: Will you need to be able to head back home on a whim, or can you commit? Think about the nearby airports.

Clocks: What is the time difference between home and your destination? Will live video calls or school prove antithetical to the rhythm of your trip?

Critters: Do you have a family pet you want to bring along?

Cosseting: What level of service will be enough, from Eloise at the Plaza with attendants 24/7 to a country-home-style setup with weekly housekeeping?

Covid-19: How does your health insurance operate? Will it cover you for illness overseas, or do you need an additional, pandemic- era policy?

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