After over two years on Zoom, corporate America is finally realizing that a post-pandemic office is more likely to have a backyard than a cafeteria. The greenlight to work from home, in many cases, translates to: Work from where you want as long as you keep the boss happy. When playing the flex(ibility) game, think bigger than a long lunch break or wearing pajama bottoms on a conference call. If nothing is holding you down, plan an escape. Working remotely can work anywhere there is WiFi.

This summer, fifteen destinations in the Caribbean want you to login to island life. From Puerto Rico to Trinidad, the region is the latest to join the co-working and co-living wandering lifestyle with the official launch of the “Work from the Caribbean'' campaign. In partnership with Airbnb, each digital nomad program has branded packages for short-termers or long-haulers up to 2 years that highlight one-off experiences, such as weekend volunteerism programs in Barbados. Work visas range from several hundred to several thousands or relocate to Puerto Rico, where of course, there are no applications, visas or passports required for U.S. citizens.

While COVID-19 restrictions prompted employers to rethink company culture, this work-anywhere-in-the-world office has outlasted the pandemic. According to the Pew Research Center, no more than 10% of the workforce worked remotely before the pandemic. After the pandemic hit, that percentage skyrocketed to 88%. U.S. travelers to the Caribbean doubled in the first quarter of 2022 compared to the same period in 2019, thanks to a huge boost of wandering millennials. Nevertheless, age is nothing but a number. Parents with school-aged children under 18 are encouraged to enroll them in public or private school in several destinations, including Belize, Anguilla, and Barbados, which boasts a literacy rate of 98%, the highest in the world .

Working remotely is convenient but it is also challenging. Studies have found that feelings of isolation and loneliness are the biggest downside. Maybe that’s why remote destination work have been growing significantly in books of 28 nights or more. Popular isles such as the British Virgin Island, St. Maarten and Antigua and Barbuda, have popular co-living spaces—usually a well-designed lodge or luxury villa—that encourage remote workers to live, work and play together like a family but with private bedrooms and bathrooms. Outsite, a global community of co-living spaces with sites in Costa Rica to France, opened its first Caribbean location on the east coast of Barbados in the village of ​​Bathsheba.

Though most of the bigger islands in the Caribbean aren’t part of Airbnb's “Work from the Caribbean'' campaign, most have their own remote work programs. Bermuda's Work & Study Remotely program has a concierge service to hold your hand through every detail of the move. Too grown to share a communal space and too impatient to sort through the Airbnb reviews? Aruba's One Happy Workcation lists hotel deals with minimum 21-nights.  The Bahamas Extended Access Travel Stay (BEATS) is still running strong after two years. Unlike other digital nomad visas which require proof of employment, the BEATS program not only allows workers but also students to study remotely from any of the country's 16 islands for up to 12 months.