What Remote Working Can Mean for New “Tourism” in the Caribbean

This article from the on-line Washington Post special travel-related section called “By the Way” <https://www.washingtonpost.com/travel/2021/02/22/digital-nomad-visas-covid/?itid=sf_travel-news&utm_campaign=wp_by_the_way&utm_medium=email&utm_source=newsletter&wpisrc=nl_bytheway > presents some of the issues that might influence the development of new tourism models, based on new work modes for several categories of worker.I haven’t seen much discussion of this in regional fora, although lately I don’t follow the many threads of the tourism press in the region.

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Like summer camp for grown-ups:
The pandemic is changing the digital nomad scene

From nomad villages to “slowmadism,” the uptick in remote work has ushered in a new wave of nomads.

(Illustration by Dan Page for The Washington Post)
By JD Shadel February 22

About 300 miles off the coast of Morocco, a tiny archipelago seems like Portugal’s take on the classic Hawaiian getaway.

For one, there’s a noteworthy cultural connection between Madeira and its Pacific counterpart: Immigrants from this autonomous region of Portugal introduced the ukulele to Hawaii in the 19th century. Then there’s the tropical volcanic landscape, with terrain ideal for hiking and mountain biking. Now, both island destinations are hoping to attract remote workers to help prop up their largely tourism-driven economies, which have struggled throughout the ongoing pandemic.

In mid-December, Hawaii kicked off a long-term stay program for 50 out-of-staters to work remotely there. Madeira, which has maintained relatively low infection rates, launched a program earlier this month that takes the concept to another level — converting infrastructure in one coastal town to launch a community for digital nomads.

[These 8 countries are accepting American travelers for remote-work trips*]

Digital Nomads Madeira Islands is akin to a summer camp for grown-ups. The program provides a free co-working space and helps find accommodations, which nomads rent privately. Organizers have dubbed it the first “digital nomad village” in the European Union.

A privileged class of workers have used the disruption of the pandemic and subsequent surge in remote work to become nomads. For some, it’s been an experience fraught with “covid grief,” “travel shaming” and even a few controversial deportations. Responsible nomads have temporarily chosen a new home base, but many are planning their post-pandemic moves. Digital nomad advocates say these new workers signal a much larger wave set to break as soon as travel restrictions ease.

“People are taking advantage of this new freedom they have to travel and work from different places,” says Gonçalo Hall, a nomad and remote work consultant who first pitched the idea of a digital nomad village to Madeira’s authorities in September.

At first, Hall framed the village as a way for struggling communities to replace lost tourism revenue. But he sees this pandemic pilot of around 100 nomads — most of whom have come from throughout the European Union, all required to show negative coronavirus tests on arrival — as the start of a growing trend.

“I think this new remote work wave will allow more and more people to [become digital nomads].” At this point, he suggests, it’s only inevitable.

The rise of the ‘slowmads’

The pandemic has accelerated several predictions that Japanese technologist Tsugio Makimoto made 2½ decades ago in his book “Digital Nomad,” one of the first-known uses of the term. In the late-’90s, Makimoto said the digital revolution would eventually eliminate the need to live near your employer — or have an employer at all.

In the case of Madeira, thousands of people from around the world have expressed interest in joining the program in Ponta do Sol — far more than the few hundred the organizers originally expected. Of those respondents, about 50 percent decided to become nomads because of the pandemic, Hall estimates.

Newer nomads say the pandemic pushed them to take a more location-independent approach to their careers — sometimes out of necessity.

“The pandemic forced me to stop and reflect on my life, and gave me the time to develop as a ‘travelprenuer,’ ” Kesi Irvin, said in an email. After covid-19 eliminated Irvin’s job as a host on sailing charters, she quickly had to pivot. As she had already built an audience on Instagram for her travel content, where she’s known as @kesitoandfro, she decided to become a full-time blogger, relocating to Budapest in September.

Pandemic travel restrictions have halted the rapid pace of most nomads. But with increasing concerns over the aviation industry’s carbon footprint, as well as the negative impact of overtourism, some nomads plan to slow their roll even when they’re able to travel more freely. It’s a travel style sometimes referred to as “slowmad.”

“I actually was never a fan of the country-hopping, fast-paced rhythm of some travelers,” Gabby Beckford, a co-founder of the Black Travel Alliance, said in an email. She is better known on Instagram and TikTok as @packslight.

A post shared by Gabby Beckford, Travel Blogger (@packslight). A year ago, Beckford quit her 9-to-5 engineering job to travel, but the pandemic kept her working remotely from her parent’s house in Virginia. At the start of 2021, she decided she “couldn’t stay home for another year,” so she relocated to Dubai. There, she says, she’s keeping an eye on the case counts. “With the vaccine rolling out,” she says, “I’m giving myself a bit of time to see how things evolve.” In the meantime, she is making a plan for what countries she might “‘slowmad’ through” once the public health conditions permit her to make her next move.
Nomad visas signal a paradigm shift

Nomads before the pandemic were mostly a niche group of millennials, many of whom promoted the #DigitalNomadLife on Instagram. They would live out of carry-on suitcases and often cross borders every few weeks, a pace set by the limits of short-term tourist visas.

This was an era of the “bromads” and the “life-hacking” popularized by self-help authors like Timothy Ferriss, who wrote the 2007 bestseller “The 4-Hour Workweek: Escape 9-5, Live Anywhere and Join the New Rich.” Ferriss preached a gospel of “geo-arbitrage” — the idea that money goes further in “cheaper” places than San Francisco or New York.

If “overtourism” defines the negative effects of an overwhelming number of tourists, then “overnomadism” seems like an apt way of describing what happened when this young class of jet-setters descended on popular destinations, from Bali and Berlin to Barcelona and Chiang Mai, Thailand. With destinations trending online and the influx of short-term rentals driving up rent, some cities began cracking down on Airbnb to tackle this brand of global gentrification.

But the economic crisis and covid-19 pandemic seems to have changed the tone in many destinations. A new category of “digital nomad visas” might make it easier for foreigners to legally stay in one place for longer periods of time. The visas also allow countries to target more mindful nomads in the process.

Last summer, Estonia became the first country to announce a digital nomad visa, which authorities believe appeals to a different type of traveler. “If you are the kind of digital nomad who would like to build long-lasting business relationships and friendships, a digital nomad visa can certainly get you into a more relaxed head space for when you approach social interactions,” says Florian Marcus, digital transformation adviser at the government agency e-Estonia.

So far, the tiny Baltic country has seen more than 10,000 people sign up for more information about its visa.

Related programs, including Barbados’ “Welcome Stamp” to Greece’s tax breaks for “digital migrants,” signal the international enthusiasm for allowing these highly mobile workers to stick around longer than most earlier nomads were permitted to. Croatia, a popular spot for nomads during the pandemic, recently approved the first foreigner, an American, for its new 12-month visa program.

“Right when the pandemic started, I was asked the question what we can do to turn Croatia into a year-round destination,” Jan de Jong says. The Netherlands-born, Zagreb-based entrepreneur wrote an open letter on LinkedIn last summer to Croatia’s prime minister. “Seeing a global trend of remote work being accelerated by covid-19, my thoughts were to start welcoming remote workers to Croatia.”

His viral post ultimately inspired the country to become among the few in Europe so far to approve a temporary residence permit for digital nomads. “Many more countries will follow,” he predicts.

Before the pandemic, Madeira’s tourism sector was booming, with more than a million annual visitors. When designed with participation from locals, nomad villages have the potential to bring in similar revenue as seasonal tourists, but with a smaller number of longer-term visitors, Hall says. He says the community partnerships might help this new wave of newbies avoid making “the same mistakes” pre-pandemic nomads commonly made such as “traveling too fast” and “not having a positive impact [on the locals].”

“These new people can learn from the more experienced people,” Hall says. “I don’t want all OGs. That would be Bali again. And I don’t want all newbies, either. That would be a weird environment. This new mixture is actually quite fun.”

JD Shadel

JD Shadel is an independent writer and editor, who covers culture, travel, technology and LGBTQ+ life. Originally from Maryland and based in Portland, Oregon since 2013, Shadel frequently travels to report stories for national and niche media outlets. Wherever they go, they always bring a can of Old Bay Seasoning.



I don’t want all OGs.

What are OGs? Old Guys?

Original gangsters, yo.


My partner and I spend a year as digital nomads in 2008-2009, and we are going to do it again as soon as we get vaccinated. It’s an incredible experience and one that I would recommend to anyone who can make it happen. Plus, it costs less than living in the US if you do it right.

My wife and I are digital nomads, we got stuck in Barcelona during the initial part of the pandemic. We hope more and more countries break out the welcome mat for remote workers.

Most countries, including the United States don’t allow you to work on a tourist visa. It’s clearly stated on the visa. Doing so can possibly put you in legal jeopardy in a foreign country if some local with “pull” complains. Then you will find out how much legal protection you will have during your trial, where the legal system might not be as transparent and honest as back home. 😉


That’s the entire point of these new programs. They allow digital nomads to work legally.

Meanwhile, doing some work over the internet in a foreign country for a short time period is really a grey area. Imagine a situation where someone is on vacation for two weeks, but answers a couple emails from work from the hotel room. Obviously that is not going to get someone in trouble. Being a digital nomad based on a country for a month looks barely different from that, from the outside, which is why in practice, basically no one actually gets in trouble that way.

Meanwhile, doing some work over the internet in a foreign country for a short time period is really a grey area.

2 days ago

Hey, I’m all for the concept of “slacking”. But it’s not free. Look at the prices they’re charging.

I’m just stating the fact that many desirable, i.e. inexpensive locations around the world don’t have special “digital nomad” visas, like Chiang Mai, Thailand, only tourist visas.

And all it takes for them to get a conviction in court is to print out your emails showing you’re working without a work permit.

But yeah, most criminals get away with crimes, especially minor ones. Good luck 🤞

2 days ago

Aren’t the work restrictions there to keep you from taking jobs within the host country? As long as you don’t overstay your visa, I don’t see what difference it makes to the host country if you are earning a living through blogging or whatever, or if you’re independently wealthy.

I’m not saying work isn’t forbidden–I’m sure you are right, and people would be wise to avoid breaking the law. I just wonder if the laws have perhaps not caught up with digital realities or if there is some reason a host country would prefer tourists to be unemployed or on vacation.

Antigua and Barbuda

Remote workers earning at least $50,000 per year can live and work on the islands of Antigua and Barbuda for up to two years through the country’s Nomad Digital Residence program. The cost to apply is $1,500 for a single applicant, $2,000 for a couple and $3,000 for a family of three people or more.

“Visa holders will be able to travel into and out of the country as they wish for the period of the visa, but will have to maintain accommodation in the country,” the program’s website states. It also notes that “applicants are not allowed to work for any entity of any kind in Antigua and Barbuda, nor to derive any income from any entity in Antigua and Barbuda.”

Entering Antigua and Barbuda requires a negative coronavirus test result received within one week of arrival, and all arriving passengers will be monitored for up to 14 days to ensure they do not develop symptoms.


The Emirati city of Dubai launched a remote-work program that allows employed people making a minimum of $5,000 per month to live and work remotely in the city for up to one year. “Tourism has reopened in Dubai thanks to safety and hygiene management across the city — with open access to hotels, restaurants, theme parks, beaches and shopping malls,” according to the Visit Dubai program’s website.

A visa fee of $287, international medical insurance and a valid passport with six months validity remaining is required to apply. Americans entering Dubai must provide a negative coronavirus test result and are subject to airport health screenings, according to the U.S. Embassy in the United Arab Emirates.

Cayman Islands

The Cayman Islands tourism department will allow remote workers who make over $100,000 annually, couples who make a joint $150,000 annually, and couples with children who make $180,000 together annually, to stay in the country for up to two years when they acquire a Global Citizen Certificate. In addition to the salary requirement, applicants must have a valid passport, a reference from a bank, a letter of employment from a company outside of the Cayman Islands, and proof of health insurance coverage. The program also charges an application fee of $1,469.

“Global citizens can begin their day with a stroll along Seven Mile Beach, snorkel with stingrays in the clear waters of the Caribbean during lunch,” Visit Cayman Islands said in a news release announcing the program. “Not to mention, remote workers have the unique opportunity to truly immerse themselves in the wonders of island life in the Cayman Islands.”


The small island of Aruba launched its One Happy Workation program in September. The remote-work visa allows U.S. visitors to stay up to 90 days by booking a package-stay program at a participating hotel, villa or condominium.

Applications are not required to book a participating stay, according to the Aruba tourism board’s website, and depending on the property chosen, “program amenities will include special rates, complimentary WiFi, breakfast, all-inclusive food & beverage options and more.” All U.S. nationals with a valid passport for their stay are able to book a “workation” with a participating property. You can browse the options, which range from hotel rooms to apartments, on the One Happy Workation website.


Launching on Aug. 1 after years of development, the Republic of Estonia’s digital nomad visa will allow foreigners to stay in Estonia for up to a year.

Applicants must have a gross monthly salary of 3,000 euros (about $3,530) or more from a remote work job to be considered for the visa, which is an extension of Estonia’s e-Residency program for foreign entrepreneurs.

“We saw that there was kind of a lack of opportunities for [digital nomads], so we wanted Estonia to solve the problem,” Ott Vatter, the managing director of e-Residency, told The Washington Post. “Estonia aims to be the hub for these kinds of new entrepreneurs that we see trending globally.”

Since the Estonian Parliament authorized the program in June, international applicants mostly from the United States, Canada, Russia and Asia completed the online request for either a Type C short stay visa, or a Type D long stay visa.

At this time, Estonia is not allowing Americans to visit the country for tourism, but they are allowed in for the purpose of work or study. On arrival, foreigners must self-quarantine for 14 days.


Shortly after reopening its borders to international travel, Barbados launched a program that allows visitors, including Americans, to stay on the Caribbean island visa-free for up to one year.

Called the “Barbados Welcome Stamp,” the program was created to bring remote workers to the country.

“The aim is to attract remote workers, with a bill to be introduced in Parliament by the government that will remove the local income taxes that normally kick in after six months,” The Post reported.

The online application fee is $2,000 for individuals and $3,000 for families. Applicants must certify they earn an annual income of $50,000 or have the means to support themselves during their time in Barbados.

Those traveling to Barbados for remote work or pleasure during the pandemic must follow new travel protocols.


On July 16, the country of Georgia announced a new program for foreigners to work remotely from the country.

“Georgia has the image of an epidemiologically safe country in the world and we want to use this opportunity,” the country’s minister of economy, Natia Turnava, said in a statement. “We are talking about opening the border in a way to protect the health of our citizens, but, on the other hand, to bring to Georgia citizens of all countries who can work remotely.”

Applicants must provide proof of employment and give their consent to self-quarantine for 14 days to be considered for the program. Applications should be available soon.

American travelers are not allowed into Georgia at this time unless they’re granted a long-term visa of at least six months, traveling for business with a special permit or are the spouse of a Georgian citizen.


Travelers from the United States are allowed to visit Jamaica. However, the entry requirements vary depending on their home state.

All Americans must have an approved Travel Authorization ahead of their trip, or they won’t be allowed to travel to Jamaica.

At this time, visitors from Florida, Arizona, Texas and New York are classified as high-risk states by the Jamaican government and are required to provide a proof of negative covid-19 PCR tests from an accredited lab to receive a travel authorization.

People who identify as business travelers in their Travel Authorization application will be given a test for the novel coronavirus on arrival to Jamaica.

“We have worked with IATA to ensure that it is a part of the airline check-in protocols that if you’re coming to Jamaica you have to produce this authorization,” said Donovan White, Jamaica’s director of tourism.

White says that while most travelers are given a 30-day visa on arrival, they can apply for a longer stay visa to enjoy more of what Jamaica has to offer digital nomads.

“There’s so much history and folklore around Jamaica. Anyone who is a nomad traveler … will be able to write a storybook about spending an extended time in Jamaica,” White said.

About Bruce

Work for sustainable development of small islands and the Chesapeake Bay; ex-Peace Corps (Volunteer and staff) in LA & Caribbean; cruised Caribbean on S/Y Meander for three years; like small tropical islands, French canals, Umbria, Tasmania, and NZ. Married 52 years to the late Kincey Burdett Potter (see Kincey.org). President of the now-sunsetting Island Resources Foundation.
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