Ditch the U.S. and Work Remotely in the Caribbean This Winter

White sands make excellent home-office decor.

Our current virtual reality of remote work and school is not nearly as mind-blowing as ‘90s movies led us to believe. So why not flip the script and augment the virtual with a tropical reality by adopting a stretch of Caribbean beach as your remote office?

With Caribbean destinations beyond eager to get their economy-driving tourism industry humming again, some places are offering incentives to get you to take that morning Zoom meeting from the beach. Many are offering expanded visa options, with resorts and hotels rolling out deals to coax you in for the long haul. Here’s how to heed their siren song and reap the high-speed WiFi in paradise. 

MORE:   Get a closer look at our favorite Caribbean destinations


The deal: Not one to let a perfectly good tourism slogan go to waste, Aruba transitioned its “One Happy Island” to the One Happy Workcation program, which invites US nationals with a valid passport to come stay on its sandy shores for seven to 90 days. 

You’ll need to purchase Aruba Visitors Insurance, which covers hospitalization, isolation expenses, and other costs should you test positive for COVID-19 during your stay. That insurance runs $10-$15 per day (and it’s free for kids under 14). You’ll also need to show a negative COVID PCR test to enter or get one on arrival. 

Once you’re here, the program requires you to book a package on the website, with condos, villas, and traditional hotel stays in the mix. Among them, there are solid deals to be had: The Digital Nomad package at Aurum, for example, starts from just $98 per night for a minimum 14-night stay. And the Renaissance Aruba Resort & Casino’s package gives 10% off the best rate while throwing in a ton of extras, like partially covering insurance costs, discounts on food and beverage, and free non-motorized water sports. 

For a 20-mile-long island, Aruba really packs it in: Your “office” breaks could include strolls on sugary beaches, kitesurfing in blue, or snorkeling below mouthwash-hued seas. Make sure you visit Arikok National Park to see eerie abandoned gold mines and swim in a natural pool hidden under the lip of a limestone cliff within the island’s most remote wilderness area.  

MORE:   20 incredible things you can only do in Aruba


The deal: Traveling to Mexico is a bit complicated—it’s a huge country, and every state is in a different situation—but the US State Department recently lifted its travel advisory against Mexico. For US travelers arriving by air (the land border remains closed for now), the country is offering a visitors permit that allows travelers to stay for up to six months. Temporary Resident Visas are also available and allow for longer stays (Viva!).

Hotels south of the border are making an appeal to remote-workers with kids in virtual school. For example, Puerto Vallarta’s St. Regis Punta Mita Resort is offering a Waldorf-inspired homeschooling program, 24-hour tech support, beachside “study cabanas,” and even study buddies for the kids while you babysit a margarita. 

Across the country in Cancun, the JW Marriott Cancun Resort & Spa is offering 10-night workation packages that include access to a private conference room, unlimited phone calls, and other perks. Vacation rentals with WiFi abound in Mexico’s popular resort towns, too, so there’s always a way to stay for longer on the cheap away from hotels, if you prefer.  

MORE:   These are the Mexico’s most dreamy beaches


The deal: Barbados reopened to international travelers in July. But the really big news for Americans this winter—when the world-class surfing is its absolute best—is the Barbados Welcome Stamp program. The special visa for remote workers lets you relocate to the islands and go about business as usual, except with the added resentment that can only come with calling into that morning Zoom meeting from Barbados.  

In addition to needing to show a negative COVID test, you’ll be required to quarantine on arrival at a designated hotel or villa for seven days, with a follow-up test after five. The program requires a visa fee of $2,000 per person ($3,000 for families). You can keep up with the island's latest travel protocols right here

Surfers should make straight for Bathsheba, the epicenter of surf culture on the island’s east coast, where you can find Airbnbs overlooking the town and rolling waves. If hotels are more your speed, guests who book seven nights or more at the Courtyard by Marriott Bridgetown near the beaches of the South Coast can take advantage of packages starting from $130 per night.

The Dominican Republic

The deal: The DR’s eXtreme Hotel might sound like a Mountain Dew-sponsored weekend, but its long-term stay option sounds like about the most laid-back stretch of work imaginable. And it’s ultra exclusive, with only 15 people allowed access per month. 

The deal invites guests to “join our bubble” with a minimum stay of two months. But with rates from $1,100 per person, per month (based on double occupancy) or $1,500 for singles, those who score a spot can do so for much cheaper than monthly rent in a tiny NY apartment. That stay includes fresh and healthy food supplied by the hotel’s organic farm and yoga in the oceanfront yoga shala. Located in the windsurfing and kitesurfing capital of Cabarete on the Dominican Republic’s North Coast, you can surf, kitesurf, and snorkel right out the door— and there’s an onsite pool and gym, too.

MORE:   While you’re here, explore the DR’s wilder side 


The deal: The Caribbean’s “Nature Isle,” Dominica began welcoming international travelers back to its verdant, volcanic shores in August. Visitors are required to complete an online health questionnaire 24 hours prior to arrival, provide a negative PCR test taken within the past 72 hours, and then do a rapid COVID test upon arrival.
If you jump through those pretty-basic hoops and love scuba diving, prepare to be rewarded at Fort Young Hotel & Dive Resort. Oceanfront in the capital, Roseau, the property is offering a WorkCation Dive Package that includes 30 nights of lodging, daily breakfast, and 11 days of two-tank diving (22 dives!) at some of the most pristine coral reefs in the Caribbean from $3,637 per person (based on single occupancy). 

MORE:   Get a primer on Dominica’s unspoiled beauty


The deal: For those looking to treat Seven Mile Beach as their break room, the Caribbean’s third-largest island is welcoming travelers from the US with proof of a negative COVID PCR test taken within 10 days of your travel date to Jamaica.  Don't expect to be wandering the island willy nilly, however—visitors must stay within the country’s “resilient corridors” that cover most of the popular vacation areas in Negril, Montego Bay, Ocho Rios,, and Port Antonio, among others. 

Once here, you’re required to stay at one of the approved hotels, villas, or guesthouses on the government’s official list of COVID-19 protocol-compliant spots. Luckily, those places include Sunset at the Palms and Tensing Pen in Negril, not to mention Hedonism II if isolation has left a big orgy-shaed hole in your heart. The Playa Resorts are running packages from $129 per person, per night, and the all-inclusive Royalton Negril lets you “Upgrade Your Office” to one with an ocean view from $1,330 per person for 14 nights. 

MORE:    The best places to scuba dive around the world


The deal: We know, we know:  Bermuda is not in the Caribbean. But it’s getting an honorary mention here since the island is welcoming Americans to a place with better winter weather than most of the US and far more cerulean waters.

Bermuda has put together a thorough guide for those looking to visit, which details the travel authorization process (and its $75 fee), as well as COVID test requirements within seven days of departure and information on subsequent COVID testing requirements once you’re on the island.  Non-Bermudians can apply for a year-long residency permit, too, detailed in the Work from Bermuda program (price tag: $263, proof of employment from your home location required). But surely you didn’t come here just to toil away at your laptop. 

For those with deep pockets, the Hamilton Princess & Beach Club is running a Feel Local, Stay a While package with discounted rates on stays over a month that start at $299 per night for one-bedroom suites. Airbnb can get you sorted for less (we found apartments starting around $75 per night), and there are plenty of other homes and villas to rent around Bermuda, too, if you prefer to avoid hotels.  

MORE:    Bermuda is even more affordable than you think

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Terry Ward is a contributor for Thrillist.