Meet the Travelers Who Are Taking Advantage of Long-term Remote Work Visas in Paradise

These adventurous travelers — some with kids — are taking advantage of their new location independence with prolonged stays in popular vacation destinations.

tropical island with yachts and houses in Bermuda
Photo: Cavan Images/Getty

If you are a globetrotter bemoaning the long pause on international travel, try setting your sights on an area of the industry that is actually growing amid the pandemic: the remote work visa. A legion of new foreign visas for full-time workers, freelancers, and digital nomads have been introduced over the last few months, offering a sundry of options for those keen on changing their lifestyles and real-life Zoom backgrounds.

Many of these palm-studded countries, like Bermuda, Barbados, Antigua and Barbuda, Aruba, Mauritius, and even the United Arab of Emirates, rely on tourism to sustain their economies, and they’ve realized they can attract long-term visitors who suddenly find themselves with the freedom to work remotely. Of course, visiting for months at a time lets you contribute to the economy without taking away local jobs for the ultimate win-win.

Pandemic or not, the concept of working remotely is here to stay, which means you’ll likely be able to try these programs for years to come. But what is it really like to live and work in paradise? We’ve spoken to three travelers who have taken the plunge to work remotely in Aruba, Bermuda, and Costa Rica. (There’s also a growing list of locales, like Estonia, Georgia, Croatia, and Czech Republic, that are offering similar long-term stay options.)

Aruba’s 3-month One Happy Workation Program

Colorful buildings in Oranjestad on the island of Aruba

If you’re hesitant to leave home for too long, a work visa program in Aruba called One Happy Workation (an off-shoot of their tourism motto, One Happy Island) offers stays of three months — a nice jump from the usual 30-day period a tourist can be admitted to the island.

Kacie Darden, owner of Blue Pineapple Travel and a Georgia resident, recently stayed in Aruba for a few months with her twin six-year-old sons. Once Kacie learned that school was going to be held virtually, there was nothing keeping them at home. Plus, she was drawn to the way the country was handling COVID-19 testing protocols and the transparency of information, with daily reports from the Aruban prime minister.

She quickly booked the plane tickets and bought insurance. “It was one of my better ideas in life,” she said. In terms of picking accommodations, Kacie only planned the first few nights upon arrival to make sure they found the right place. She advises that people remain flexible at the onset.

“Working remotely is all about Wi-Fi. I needed to be able to handle three Zoom meetings at a time, and we did bounce around at first to some condos and timeshares. We even stayed at an all-inclusive for a few nights and joked that it was a vacation.”

Where Kacie and her boys did end up for the majority of their trip was a boutique hotel called Boardwalk, home to cheerful casitas owned by another set of twins named Kimberly and Stephanie. “It was just perfect. It had a homey vibe and enough of a kitchen to feed hungry six-year-olds,” she said. “Plus, I needed a few more amenities than just an apartment.”

A typical weekday would start with breakfast on the patio. Then, Kacie would set up her boys with virtual classes while she worked in another area of the casita. They’d take short walks to get some sunshine and then push through the school day, which lasted from 9 a.m. to 3 p.m. Kacie said, “That was going to be my challenge at home or in Aruba. I’d rather be in Aruba.” At 3 p.m., they’d change clothes and run to the beach and stay until sunset. Kacie would make the boys dinner and put them to bed, and then enjoy some quiet time to finish her work.

Perhaps the best part of the schedule was having a Monday through Thursday routine. “If living in a vacation destination, we at least needed to have three-day weekends. So, I truncated the workweek”, she said. They made lists of beaches and would spend weekends touring the island. “One of my sons made it a mission to see all the beaches in Aruba.” Kacie’s husband, who works as a professor, also came for a weeklong visit.

As for the shorter time frame, Kacie said that two months was about long enough for them. “I think it’s ambitious to leave for an entire year with little ones, and this wasn’t as big of a leap. But once you’re home, you start thinking 'Oh, we could do that again.'” Costa Rica is on the table and they’re also thinking about Marrakech.

“The best thing about these extended vacations is that you don’t have to do it all in a week. You don’t feel rushed. You can try one or two things at a time and revisit your favorites.”

Bermuda’s 1-year Work From Bermuda Certificate

tropical island with yachts and houses in Bermuda
Cavan Images/Getty

One of the first new visa programs for remote workers came from Bermuda, catching the interest of British and North Americans wanting to spend a year surrounded by coral reefs and pink-sand beaches.

Even during a phone interview with a potential oncoming hurricane (thankfully, Hurricane Epsilon veered away before hitting Bermuda), Carole Reed is enthusiastic about her new living situation.

The New Yorker and her family moved to the island in September to live in a cottage on Coral Beach, right in time to enroll her 16-year-old daughter at a local school there. The situation worked well for this family because Carole’s 17-year-old son chose to continue virtual learning through his own New York school. Meanwhile, Carole and her husband work remotely — as the New York art editor for Amazing Magazine and a chief marketing officer, respectively.

A typical day for Carole starts with getting her daughter to school on a moped — she jokes this experience is an adventure within itself. She then returns to Coral Beach to squeeze in a workout before getting her son situated with his online learning. Her husband works at his desk in the master bedroom, and Carole works in a makeshift office outside of the kitchen.

It’s not all work and no play, though. The family makes it a routine to head to the ocean for a swim twice a day. “It’s awfully nice to take lunch on the beach, and my son, husband, and I are like little kids when we get to walk a short distance to a powdery beach and go for a swim,” she said. “I almost feel guilty that it’s so beautiful.” (The second swim of the day occurs when her daughter returns home from school.)

Though Carole says she misses autumn in New York, she and her family have met some friendly expats in Bermuda. Between tennis matches and thermoses of Dark and Stormies on the beach while maintaining social distance, she said, “It’s an amazing culture of transplanted workers.”

When asked if she felt safe exploring Bermuda, Carole explained the strict quarantine procedures. “Everyone is very respectful — they wear masks and make you sanitize your hands before entering a public space. It’s non-politicized protection and communal care for everybody’s health and well-being,” she said.

“I still feel like I’m on vacation. Every weekend, we’ve tried to take a hike or discover something new.”

Carole said the family plans to stay until February and probably longer. “We love New York as a city and hope that it does well through the pandemic. But being in the tropics with some really nice people, I am not regretting this decision at all.”

Costa Rica’s 2-year Rentista Visa & 3-month Tourist Permit

beach in the town of Jaco, Costa Rica

If you’re a freelancer and want to fly under the radar as a tourist, Costa Rica may be the answer. The country does have a visa program for foreign nationals called Rentista, which grants temporary residency for remote workers, but Soraya Caliva, owner of Casas de Soleil in the surf town of Santa Teresa, says that most of the people who are living and working in the country are not on this visa program. “It's not an easy one to obtain, unless you have the means to keep $50,000 sitting in a local bank account at all times as a bond,” she said. “I believe what you will find is called the perpetual tourist — the ones who have to leave the country (say by driving to Nicaragua) every three months to re-stamp their passport.” Luckily for these tourists, she explained, Costa Rica passed a law stating that anyone who came into the country last December did not have to leave since borders were closed due to the pandemic, giving an automatic extension to their tourist permit.

Whichever way you enter Costa Rica to work remotely, Santa Teresa is no stranger to digital nomads. Clifford Ochser, founder and owner of a stargazing tour company in Sedona, Arizona, said, “I have been a remote worker for the last four years, traveling the world after running my U.S. tour business on-site for 16 years.” In March, Clifford was in Prague and had to decide where he wanted to spend the pandemic. After traveling to Santa Teresa many times in the past, there was no choice to be debated. “It was the best important decision I have made in a long time,” he said.

Clifford said that this area of Costa Rica was a favorite: “I’ve developed friendships and social circles, and it’s such a healthy place to be.” And he landed just in time. “I was on a plane, and two days later, they closed the border,” he said. “I just love it here. There are people all around the world who live here and that makes it very interesting.”

A typical workday for Clifford in Santa Teresa starts online with confirming customers, responding to inquiries, looking at forecasts for tour locations, sending status updates, and making sure his staff is set up properly. “By noon, I’m mostly free, so I usually go for a long walk on the beach and swim in the ocean. I also like to support some of the restaurants, talk to the business owners, and check in with some people who are here in town,” he said. “Those of us who are somewhat blessed, it’s our responsibility to help others, to encourage and support others, particularly locals who are trying to make it work.”

As for finding a temporary home, Clifford became familiar with Airbnb markets and found that hosts were open to negotiating prices for a longer stay, especially after realizing that short-term tourists weren’t coming back for a while. Consider a three-bedroom house on two acres with a saltwater pool for $800 a month, or a large studio loft with an expansive view of the ocean for $1,000 a month. “Normally they would go for $200 a night,” said Clifford.

He also went on to explain that Santa Teresa probably has an advantage with strong Wi-Fi infrastructure because of the people who live and work here. “Santa Teresa is unique compared to other places I’ve seen in Costa Rica. The economy is open and people are still spending money. There’s an energy in the town...and people are out and about,” he said.

As for going home, Clifford has no plans to return anytime soon. “Because I’ve been traveling for so long, my home is where I am,” he said. “We create our home and our circle of people and support system wherever we are. Longer stays give you more flexibility to sort of plug into the community.”

Clifford said he talks to his friends who would love to get out of the country, but they’re still reluctant to make it happen. He added, “There’s a fear that’s pervasive and a lot of uncertainty. It’s going to be interesting to see what develops, particularly with the U.S.”

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