Jetblue Vacations Will Now Pay $500 if It Unexpectedly Rains on Your Trip to Jamaica

“In 2025 we partnered with WeatherPromise to introduce rain protection for JetBlue Vacations packages, which gave customers the option to add that coverage when booking,” says Jamie Perry, President of Paisly, the company that runs JetBlue Vacations. “This program takes that idea a step further by building the weather guarantee directly into eligible Jamaica packages.”

JetBlue Vacations first teamed up with WeatherPromise, a travel insurance–esque company that pays out for inclement weather while traveling, in February 2025. It was the startup’s first airline partner and gave customers the option to add rain protection when booking a combined flight and hotel package. However, the new Jamaica guarantee is different, as it’s already included in eligible bookings and tied to a specific destination.

Boats off the coast in Negril, Jamaica. Photo: Tom Podmore/Unsplash

Starting with Jamaica was a natural fit. “Jamaica is one of the most popular destinations our customers book through JetBlue Vacations, and the Jamaica Tourist Board was interested in trying something new to encourage travelers to visit,” Perry tells Matador Network. “Caribbean travelers know quick tropical showers happen, so the idea is to remove some of that uncertainty when people are deciding to book, especially as we move into the summer season when showers can be more common.”

The technology behind the weather guarantee is high tech. WeatherPromise pulls data from multiple sources and agencies, including NASA, NOAA, and the international European Centre for Medium-Range Weather Forecasts, as well as thousands of weather stations, radar reports, and satellites. The announcement claims it can accurately pinpoint weather within a four-kilometer range, allowing each guarantee to be tied to weather at the traveler’s selected hotel, not the destination as a whole. According to information shared with Matador Network, WeatherPromise considers 439 million weather measurements per day, and can even issue payouts before bad weather happens, if it’s looking likely.

Crucially, the weather guarantee doesn’t issue payouts based on any amount of rain. Instead, it issues a $500 credit if rainfall exceeds the forecasted amount. After booking a trip, travelers will get access to a personalized dashboard so they can monitor predictions in real time. If it rains enough to meet the threshold, travelers will get a notification on the dashboard, requiring them only to click to confirm the payout. What triggers a payout varies based on each trip, but JetBlue Vacations told Matador Network it’s usually based on the number of hours of rain above a certain intensity (for example, more than 1 millimeter of rain per hour), though it varies by location and dates.

Photo: JetBlue Vacations

Travelers must book a flight and hotel package via JetBlue Vacations between three and 16 nights long, and trips must be booked by May 31, 2026 — though travel can happen any time before December 1, 2026. The point of entry must be either Montego Bay or Kingston, and trips need to be booked at least seven days in advance. Currently, there are more than 90 hotels available in Jamaica via JetBlue Vacations, and flight options include all major airlines, not just JetBlue

While Jamaica is currently the only destination with such a promotion, Perry says the company is already eyeing expansion. “This is the first time we’ve integrated a destination-specific weather guarantee into a vacation package, and we’re watching closely to see how customers respond,” he said. “We think there’s potential for other destinations to explore similar programs, particularly during seasons when travelers may be hesitant because of weather.” They’re even working on adding a similar weather guarantee to the company’s cruise offerings, he says.

JetBlue Vacations is currently the only airline vacation brand with a WeatherPromise partnership, with WeatherPromise available in 70 countries across six continents.