Explore Being a Digital Nomad

So, you want to be a digital nomad in the Caribbean?  You could! Some countries have developed carefully crafted options to offer a place to work or study remotely while enjoying the island, the culture, and some additional benefits.  If you already work remotely and generally make more than $50,000 annually, you could spend a year or two working from a Caribbean island, sounds dreamy doesn’t it? 

You can bring the whole family too! Most allow you tax free benefits as well, the ability for your children to go to school (typically a private one, not the public ones).  During that time, you can freely travel back home as needed, also. 

Each country has different fees and processes but here’s a highlight of where you can go and how to find out more. For checking internet availability, try https://isp.today/

digital nomad checklist infographic 1

Make emergency Back-up plans (natural disasters, health issues) because things happen.

Find local nomad groups to join (facebook, reddit) to learn what you don’t know that you don’t know.

Paradise may not be as open as you hope, there could be other restrictions still in place that govern how you can shop and what amenities are available to you.

Keep in mind that if you don’t follow the rules, your visa can also be revoked.  Be mindful and respectful and you should have a great adventure.

carib nomad 2 pin this
(Reserve on Tock)

1.   LondonHouse – 21st & 22nd floors

85 E Wacker Dr, Chicago, IL 60601

I know how important it is to book early and still it slipped my mind until a week before our trip.  At that point, the only thing I could reserve was an 11AM table on Thursday.  The weekend was already sold out a week before.  Probably the most popular one we went to, I managed to score a sunset booking when they called to confirm my reservation.  Yes, always ask for what you really want when you have the opportunity.  Be sweet as sugar and you might just get it. 

My 11AM time ultimately was cancelled due to rainy weather.  The rooftop was closed.  I still had hope for my sunset time.  Another miss though, we sat in the restaurant for a little while, then up to the rooftop to take some pics.  My hopes for this iconic sunset on the river were dashed.  But the drinks were good, service was okay, and I did get to see the rooftop, so the goal was accomplished.  I ordered a second drink – French Martini but it never showed up and I didn’t bother asking for it again.

Overall, it’s a bit more pretentious and definitely turns into a club setting on the weekend with people waiting in line for the elevator.  One elevator becomes designated for this with a host stationed at the beginning of it.  If you are staying at the hotel, no worries, that line does not affect your ability to get to your room.


Casamigos Blanco, Green Chartreuse, mango,
habanero, chipotle powder

Islands to Explore


Dominica has created the Work In Nature (WIN) Extended Stay Visa which allows you to relocate there and work remotely for up to 18 months.  You can go solo, with your family, or with a business team.  Your children can attend schools. 


  • Income tax waiver
  • Duty Free concessions on imported personal effects
  • Ability to apply for an annual driver’s license
  • Travel freely during visa period


Application Fee (non-refundable): US$100

WIN Visa Fee

Single Applicant: US $800

Family Application: US $1,200

One Business, Multiple Applicants: US $800 plus US $500 for each additional employee for a business applying for four or more employees

Stay: Citrus Creek Plantation offers a 2BR villa for about $150/nt. https://citruscreekplantation.com/

Internet: Up to 100Mbps


Work from Anguilla


91 days up to 12 months


+ US $3,000.00 (4 persons)

Main applicant + three(3) dependents

+ US $250.00 for each additional family member.

1 head of household, 3 dependents (spouse and 2 dependents)

A dependent:

  1. A child or step-child under the age of 26 years
  2. any other relative who is, by reason of age or any infirmity of body or mind, wholly dependent on that person for his/her subsistence.

Stay: Find a Vacation Rental in Anguilla

Internet: Up to 32Mbps home internet; up to 100Mbps via satellite


Montserrat Remote Worker


  • Works for an employer that is registered in a foreign country and they have a contract of work with that employer; or
  • Conducts business activity for a company that is registered in a foreign country and of which they are a partner/shareholder; or
  • Offers freelance or consulting services mostly to clients, whose permanent establishments are in a foreign country, and with whom they have contracts; and
  • Earns an annual income of USD$70,000; and
  • Has health insurance with valid Montserrat and COVID-19 coverage.


Up to 1 year.


Application fees are required before application processing. These fees are nonrefundable.

Single Applicant


Families (up to 3 dependants): USD$750

Additional family member: USD$250 each

Stay: Available apartment rentals can be found for as low as $75/night. https://www.visitmontserrat.com/apartments/

Internet: up to 100Mbps via satellite


@Home in Curacao


up to 6 months (plus a possible 6 month extension).


About $294

Stay: Find a Vacation Rental in Curacao

Cayman Islands

Cayman Global Citizen

Requirement: Must make a minimum of $100,000 annually


up to 2 years


Global Citizen Concierge Certificate Fee up to Party of 2 persons: US$1,469 per annum

Global Citizen Concierge Certificate Fee for each dependent: US$500 per dependent, per annum

Credit Card Processing Fee: 7% of total application fee

Stay: Find a Vacation Rental in Cayman

Internet: Generally, up to 10Mbps; up to 100Mbps via satellite.


Work From Bermuda


  • be at least 18 years old and pay the application fee
  • not have been convicted of a crime in Bermuda or elsewhere
  • possess valid health insurance coverage
  • demonstrate employment with a legitimate company or your own company registered and operating outside of Bermuda, in the case of a remote worker
  • provide evidence of enrollment in a Research, Undergraduate, Graduate or Doctorate Programme, in the case of a student
  • have substantial means and/or have a continuous source of annual income


up to 1 year


Application $263

Yes, family members will need to apply separately and pay a separate fee. An income earner with dependents should submit one form for each family member. All related applications must be submitted on the same day.

Stay: Find a Vacation Rental in Bermuda

Internet: speeds up to 500Mbps through ONE Communications

from remote worker to digital nomad


Bahamas Beats


up to 1 year


Application $25

Work Remotely Permit $1000 for head of household & $500 for each dependent

Study Remotely $500 each

Travel Health Visa required

Stay: 2BR waterfront villas start at $225/nt or $1400/wk at Paradise Cove

Find a Vacation Rental in the Bahamas

Internet: May find up to 70Mbps (home internet) or 100Mbs (satellite)


Work from Barbados

See Visa & Entry Requirements


Up to 12 months


$2,000 Individual or $3,000 FamilyApplication $263

Yes, family members will need to apply separately and pay a separate fee. An income earner with dependents should submit one form for each family member. All related applications must be submitted on the same day.

Stay: Find a Vacation Rental in Barbados

Internet: Barbados has high-speed fibre internet with download/upload speeds up to 1,000/500 Mbps and 4G mobile services.

Antigua & Barbuda

The Nomad Digital Residence visa offers you a chance to visit 365 beaches, a beach a day.


Up to 2 years.


SINGLE: USD $1,500.00;

COUPLES: USD $2,000.00;

DEPENDENTS (Family of three persons and over): USD $3,000.00

Stay: Find a Vacation Rental in Antigua & Barbuda

Internet: May find options up to 100Mbps via satellite

Short Term: Aruba


One Happy Workcation


From 1 week up to 90 days.


No additional fees or documentation, only requirement is a US passport and complete the online ED Card.

Purchase Aruba Visitor Insurance.

Stay: Discounted pricing for participants in One Happy Workcation

Internet: Up to 150Mbps via satellite

An extended stay in the Caribbean sounds nice, think of all the wandering we could do.

Ready to Wander?

Book a Hotel or Villa

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Happy Wandering!

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