Let’s face it: There aren’t many times in your life when you can actually pack up and go somewhere for a month or a year and not pull the kids out of school or take a sabbatical from work. Some might say that one of the silver linings of this COVID-19 pandemic is that it’s allowing people to work and go to school from wherever they are and destinations are capitalizing on it.

Barbados Welcome Stamp
The first destination to come up with this genius marketing idea was the Barbados Government, which, in late June, announced the introduction of the 12-month Barbados Welcome Stamp. This new remote work program establishes a visa to allow people to work remotely in Barbados for a maximum of 12 months. The visa is available to anyone who meets the visa requirements and whose work is location independent, whether individuals or families. It costs $2,000.00 USD for an Individual visa or $3,000.00 for a Family Bundle. Here’s how to apply.

Bermuda’s One (1) Year Residency Certificate Policy
Bermuda is just a 90-minute flight from New York and most eastern cities but it feels a world away, with the friendly people and beautiful beaches. Visitors may stay in Bermuda from 90 to 180 days, have valid health insurance, demonstrate sufficient means and be over 18. The cost of the certificate is $263.

Aruba’s One Happy Workation
Aruba is another Caribbean island that is offering a visa where Americans can stay for a week or up to 90 days. Aruba is offering discounted rates on accommodations and many of the packages come with some special “extras”, including discounts on experiences and local activities.

Antigua and Barbuda Has a New Two-Year Residency Program
The dual-island nation of Antigua and Barbuda launched a new “Nomad Digital Residence Programme” for those whose employers are based outside the islands. Here are the details.

Working From Home in Anguilla
Anguilla arguably has some of the most beautiful beaches in the world, at least that I’ve ever seen. Like some of her sister islands, Anguilla is now going after the Work from Home (WFH) community. The government of Anguilla is inviting you to consider changing your status to WFHiA (Working From Home in Anguilla) and is making an irresistible offer to trade in your humdrum home office for a Caribbean island nirvana – applicants who meet the requirements can work and live in Anguilla for up to 12 months. Here are the details along with the other islands and countries offering people to stay long term.

Estonia’s Digital Nomad Visa for Remote Workers
Ah, the country where my wife lost her passport and made me sweat like never before! (They were about to issue her an emergency passport and put her on the next flight out!) But I digress. You can apply for Estonia’s digital nomad visa if:
-You are able to work independent of location
-You can perform your work duties remotely using telecommunications technology
-You either have an active employment contract with a company registered outside of Estonia, conduct business through your own company registered abroad, or work as a freelancer for clients mostly outside of Estonia.
-You can provide evidence that your income met the minimum threshold during the six months preceding the application. Currently, the monthly income threshold is €3504 (gross of tax).

If interested, fill in the application form and pay the 80€ state fee for a Type C (short stay) visa or the 100€ Type D (long stay) visa. Then make an appointment at your nearest Estonian Embassy or Consulate to submit your application. Make sure you bring copies of any required supporting documents.

Jamaica doesn’t have a formal policy but they do allow for 30-day visas that can be extended once on the island. The cost for an application is $98, according to Afar Magazine.

Mexico doesn’t have a formal policy either but according to Forbes, “travelers—including digital nomads—can stay Mexico, visa-free, for up to six months on a tourist visa. But it’s possible to obtain a Temporary Resident Visa that allows you to stay in the country for one year and even extend it up to three times. You will just need to apply for this special visa before your trip and show proof of a certain amount of income.”

Remotely From Georgia
I’m not talking about the state of Georgia, I’m talking about the country that shares borders with Turkey, Ukraine, Armenia, Azerbaijan and Kazakhstan. They are offering travelers a remote working program. According to TimeOut, “to take advantage of it, all you have to do is fill out an application form (requiring personal information, a certificate of employment and a letter of consent to undergo a 14-day quarantine) and obtain a ‘preliminary confirmation’. You’ll then have to quarantine for a fortnight at your own expense and provide proof of travel insurance that lasts at least six months.” The program started in late August and is open to people from 95 countries.

If you have the job and the means and are working remotely, then why not turn lemons into lemonade? If you’ve ever wanted to live in another country or escape winter, then you might want to seriously consider taking advantage of these crazy times and the offers presented by these countries. I’m fortunate that, with the exception of Georgia, I’ve been to all of the countries listed above. I really want to go to Georgia because I hear it’s beautiful and a bargain. But my first choice out of the options on this list would be Barbados, followed by Bermuda. How about you?

4 Comments On "How To Live and Work In Paradise This Winter"
  1. Penny|

    I’m thinking Barbados as welll. Have you been before?

    1. Johnny Jet|

      I have! I took that pic. It’s amazing place

  2. Todd Merkel|

    Great info!! I’ve know about the digital nomad visa, but the others were knew info:

    Thanks again, and hard to believe I’ve been following you for close to 20 years, since moving from Philly to Portland. All the best to you and your beautiful family!!

  3. Liz Perry|

    How about winter sports destinations? Juneau AK has a terrific city-owned ski area just a few minutes from downtown, lots of places to cross country ski, snow-shoe and hike. Great food, arts, and cozy places to stay. Just sayin’. : )

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