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WF Caribbean. What It’s REALLY Like to Move to a Paradise in the Middle of a Pandemic

What it’s like to move your WFH setup to the Caribbean.

Ashley M. Hunter has stopped doing Zoom calls outside with the Atlantic Ocean to her back. It was making too many people jealous. The 41-year-old insurance executive has been working from Bermuda for the past seven months, thanks to a COVID-spurred residency program on the island.

Bermuda is one of a handful of spots in the Caribbean inviting gainfully employed international visitors to come and stay for a while. With few people going to an office every day, remote work possibilities have gone international.

Idyllic islands in the Atlantic Ocean, including Anguilla, Aruba, Barbados, the Cayman Islands have implemented temporary residency programs amid COVID-19 as a way to help keep the economies afloat while tourists stay home, waiting out the pandemic.

If it sounds too good to be true, consider the barriers to entry: fairly high, nonrefundable application fees for many of the destinations; an annual income requirement for acceptance—in Barbados, it’s $50,000, for the Cayman Islands, it’s $100,000 (along with a slew of other requirements); plus the cost of island living in addition to expenses attached to one’s permanent residence.

A New Digital Nomad

In essence, many of these programs are turning the digital nomad lifestyle as we once knew it on its head. Participants aren’t international backpackers hoping to scrape by for as many months as possible on the road, hopping from one place to the next.

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Glenn Jones, Bermuda Tourism’s Interim CEO, says he’s been surprised by “the share of people on this program who are senior executives, directors on boards, owners of their own companies, founders of their own companies.” It doesn’t fit with his previous understanding of a digital nomad, but that’s not necessarily a bad thing for the island.

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What these digital nomads share with their predecessors, however, is a sense of community. A participant in Barbados’ “Welcome Stamp” program, Mita Carriman launched a community for digital nomads there called Bajan Nomad Social.

The former business and IP attorney isn’t new to working remotely from cool locales around the world. Carriman, now CEO of Adventurely, tried on the digital nomad lifestyle in 2017, and since then has lived and worked in 13 different countries.

She spent six months in Barbados, the first country she ever visited with her Caribbean parents, and would recommend it to anyone, especially first-time nomads. Carriman, who has since moved on to Mexico, says Barbados was a bit on the expensive side but adds, “It was worth it to experience the culture, safety, and perks around and about the island.”

Like Hunter, Carriman has actually been working. She points out that “digital nomads aren’t on vacation” and for the most part are “exceptionally responsible and disciplined people.”

“It was worth it to experience the culture, safety, and perks around and about the island.”

Hunter, who says she’s in the process of starting an insurance agency in Bermuda, says she chose the country because she thought it would be good for business. Her instincts were right, it was.

Likewise, for Georgia resident Kacie Darden, 37, taking part in Aruba’s One Happy Workation program meant moving her workplace to the sunny Caribbean island. The temporary set-up had Darden, the owner of boutique travel agency, Blue Pineapple Tours, and her twin six-year-olds maintaining a fairly similar work and school schedule Monday through Thursday. With her academic husband dealing with duties on campus, Darden and her boys looked at the temporary Aruba relocation as “a bright spot in an otherwise difficult time.”

“We often had three Zoom calls going at the same time in different parts of our living space!” Darden says.

Vacation Privileges

Although work factors into these digital nomads’ lives, there’s also room to play.

What the participants in the Caribbean island programs also have are what Carriman describes as “vacation privileges”  which they “absolutely indulge in once they responsibly get their work done.”

Darden says she and her husband George called the family’s two-month-Aruba stay the childrens’ “first grade study abroad program.”

Fridays they saved for field trips, says Darden. “We spent time taking care of animals at the Donkey Sanctuary or we took a tour at the Aloe Factory. We went on hikes and visited the ostriches and emus at the Aruba Ostrich Farm. One of my twins was determined to see every beach in Aruba, so we did our best to find them all during our long weekends.”

Eusi Skeete, US Director of Tourism in Barbados, says the island’s beaches have been a draw for participants of their Welcome Stamp Program, but Carriman insists living and working in a beautiful remote location isn’t license to lounge at the beach all day.

“You work during the day, you prioritize your deadlines, and then you make the most of your free time and weekends when and how you can,” says Carriman, who admits that Barbados’ “beaches truly are something to be rivaled.”

“We offer remote workers the backdrop of idyllic beaches, tropical landscape, work-life balance, and the opportunity to still be earning their global salary,” says Skeete, who says he cannot provide an actual number of “welcome stampers” but notes that hundreds have been accepted and arrived from the United States, United Kingdom, Canada, and Ireland.

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When she doesn’t have video calls and the weather is nice, Hunter works outside, overlooking the water. She also starts every morning with a cup of coffee on the dock within walking distance of her flat. She watches the sun rise and then gets down to business.

Also taking advantage of the spectacular Caribbean sunrises is Ryan M., an attorney from Chicago who has asked that we withhold his last name for privacy concerns. Ryan is participating in the Cayman Islands Global Citizen Concierge Program (GCCP). After watching the sun rise, Ryan begins his workday—on the beach. “In the middle of the day I hit the gym, and then I usually make it back in time to catch the sunset at night,” Ryan says, describing an average day.

Island Time

Both Hunter and Darden reference the pace of life on the islands—slower than back home in the States—as being a plus.

Darden appreciated the ability to travel slowly, something not typical in the family’s traditional vacations. “We had a list of things we wanted to do, but we never felt rushed to see everything or do everything at once. The gift of time allowed us to slow down and take in each place so much more deeply than on a traditional vacation.”

People still work a lot in Bermuda, explains Hunter, who notices a slower pace reminiscent of the South, where she’s from.

Ryan’s work can be overwhelming, and he credits the gorgeous Cayman setting with helping him manage stress. He looks up from his laptop, takes in the ocean and serene backdrop of the island, and is able to “both connect and unplug when and where I need.”

10/10 Would Recommend

The Darden Family left Aruba on October 4 after two months and a day in paradise. They returned for a week in January, giving the Aruba economy, which is highly reliant on tourism, yet another little boost.

Darden would recommend the change of scenery to anyone. Likewise, Carriman says she’d recommend the Barbados residency program, which she says exceeded her expectations. Ryan M. had never been to the Cayman Islands before but is thrilled with the experience. He, too, would recommend it to anyone who has the ability to work remotely. “On top of being an absolute paradise, Cayman’s handling of the COVID pandemic is greatly appealing,” Ryan says.

If you have the means, Hunter says, Bermuda “is not a bad place to ride out the pandemic.” In fact, she likes it so much she’s considering what it would look like to split her time between New York and Bermuda.

chispy0203 March 16, 2021

When did they move Bermuda from the North Atlantic to the Caribbean?