Have Cards, Will Travel

Working from home in a hammock

How working remotely on a tropical island is possible – with the right precautions


For many, working from home is becoming the new normal. But what if your definition of “home” changed? Relocating to a tropical island the rest of 2020 might be a nice way to change your surroundings – as long as you take the proper precautions.

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While international travel is still mostly not in the cards for this summer, with many borders remaining closed to U.S. travelers, our neighbors in some of the Caribbean islands are beginning to crack their doors open to Americans.

While I’ve been trying hard not to get myself too excited about making future plans I’ll have to cancel, I have to confess that I’ve done a lot of daydreaming this week about napping in a hammock between two palm trees overlooking the Caribbean Sea.

Let me back up and tell you that back in January, I decided that 2020 was going to be my year to see the Southern Caribbean. You obviously know how this story ends, but what you might not know is that before COVID-19, I spent most of the month of February working remotely from three tropical Caribbean countries I’d never been to before: Barbados, Trinidad and Tobago and St. Vincent and the Grenadines.

Writing from a beachside hammock in Barbados in late February, I shared with you all my discovery of Trinidad’s Carnival. The following week, I’d planned a follow-up story to share secrets on navigating the lesser known Caribbean islands on rewards points – but instead I wrote about canceling a trip to Italy, my first COVID-19 travel casualty.

It has been difficult to get excited about international travel when it still seems very far away, but I’ve kept positive by focusing on what we can do to keep earning points and safely travel this summer. That was, however, until an announcement last week from Barbados awoke my wanderlust and all those Caribbean travel tips came rushing back.

Last weekend, the country of Barbados began reopening to international travelers and their government announced they have been exploring the possibility of a new, yearlong visa called the Welcome Stamp, which enables visitors to remotely work from the country.

As someone who regularly works from her hammock or a hotel, the proposition of getting a visa to work from Barbados for a few months is a very tempting alternative to the rainy, socially-distanced short days of an Oregon work-from-home winter. Yet, while I’m super excited that my Southern Caribbean goal might get to be resurrected, the biggest opportunity I see here isn’t really for digital nomads like myself.

According to data from Global Workplace Analytics, only 3% of U.S. employees worked from home full-time or more than half-time pre-COVID. Post-COVID forecasts predict many businesses will not call their employees back to the office, bringing that number to 25%-30% of remote workers.

What does this mean for you? If schools remain shuttered come fall and your job can be done from your laptop, you could go live out the remainder of 2020 on a tropical island. You might even forget that you spent the first five months of the year on your couch.

If you’ve read this far and are interested in checking out Barbados, here are a few practicalities for remote working on your rewards points (hopefully you’ve saved a lot of them while not traveling).

See related: Planning a socially-distanced summer vacation

Research the risk factors

Before I give you details about planning international travel, I must in good conscience remind you to consider the risks to you as well as to the communities in the places you visit when traveling during COVID-19. Please be responsible of yourself and respectful of others.

Barbados and the other Caribbean countries opening to international visitors have stringent entry regulations to help keep everyone safe. You’ll have to have a negative test before travel and proof of insurance, have your temperature taken on arrival and you’ll have to wear a mask in public spaces – even in the tropical humidity.

As a responsible traveler, and a respectful guest, you’ll also have to remember that you’re opting to live on an island as a visitor where medical care is limited (even for locals) and all of the resources (other than what grows on the island) are imported.

Also, remember that hurricane season in the Caribbean is from June 1 to November 30.

Getting there on points

You’ll want to use either your JetBlue or American Airlines points to get you to Barbados Georgetown International airport (BGI). JetBlue resumes commercial flights from New York’s JFK at the end of July, and American is selling tickets to BGI for flights from Miami (MIA), beginning August 5.

On AA, economy-class award tickets start at 15k points (plus $12.70 in taxes) for a one-way, or 25k each way for first class if you want to ensure extra space and a place in front of the immigration line.

JetBlue award tickets have more variable pricing, starting at 13.5k TrueBlue points (plus $7.10 in taxes) for one-way economy. As of July, JetBlue is still blocking middle seats as much as possible to provide distancing on planes.

If you haven’t been earning on a TrueBlue credit card, American Express Membership Rewards points transfer to TrueBlue at a rate of 250:200. While I normally try not to transfer Membership Rewards points to U.S. carriers because of taxes, one bright spot of COVID is that Amex has waived all point transfer excises taxes through Dec. 31, 2020, in response to the Coronavirus Aid, Relief, and Economic Security (CARES) Act.

See related: Which JetBlue credit card is best for me?

Finding a remote work home

If you’re just looking for a place to stay for a week or two in Barbados, there are a handful of points hotels on offer, including a Marriott Courtyard right across from the beach in an active area of town that is walkable to a supermarket. There’s also a more secluded Hilton on the point with a resort feel and a Radisson that sits on the most popular white sand beach on the west side of the island.

In my professional travel opinion, all three of these hotels are pretty mediocre – while pretty pricey in points. For a shorter COVID break, I’d recommend a boutique hotel (booked with points through Chase Ultimate Rewards) or a vacation rental on a quiet part of the island.

For a longer-term remote work base, the best option would likely be a local rental. Book yourself into an Airbnb or one of the points hotels for a few days, while you give yourself some time to explore the island and see if you can hire something out locally.

You’ll likely be able to find something at a lower price and you’ll be sure to land on a part of the island that matches your vibe. During my February visit, I met plenty of windsurfers who had been renting out homes on the south part of the island near Silver Point on monthly rates.

While we will have to wait and see if remote work visas will actually happen (and if borders that open this week will still be open next month), these small steps in reopening rekindle my hope as a traveler. Maybe I’ll see you working on a Barbados beach in November? Fingers crossed we’ll have safe options for dusting off our passports soon.

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