American Airlines to reintroduce evening flights on trial basis

The once-popular American Airlines evening flight from Miami to Grand Cayman will return later this year for almost one month.

The Cayman Islands Department of Tourism announced the reintroduction of the “overnight” route in a press release on 28 May, saying that beginning 6 Oct. 2025 and running through 1 Nov. 2025, the daily flight from Miami will arrive in Grand Cayman in the evenings at 7:05pm and depart from Grand Cayman the following morning at 8:30am.

Reached for comment about the reintroduction of the evening flight – which was a regular and popular part of American Airline’s service to Grand Cayman prior to the COVID-19 pandemic – Cayman’s Director of Tourism Rosa Harris was undeterred by the fact that the route would return for a short time during what is traditionally a slow period for tourism.

“I like to look at this as the glass half full; this is more than we had yesterday,” she said with regard to the added airlift.

Harris said she was looking at the route as a “pre-season trial” in advance of the 2025/26 winter season. Her hope would be that the route proves successful enough for American Airlines to make it permanent.

In addition to increasing the airlift numbers, the route is beneficial in two specific ways: It aids in allowing same-day connections through Miami and gives Cayman Islands’ residents increased options for travel to that city.

Convincing American Airlines to reintroduce the route was a team effort that culminated with several stakeholder teams, including Harris and the Department of Tourism, lobbying Jose Freig, the airline’s vice president international operations, during the combined CAPA Airline Leader Summit – Americas and the GAD Americas Summit hosted by the Cayman Islands on 2-4 April 2025.

Harris said that during a one-hour meeting, the group presented a “united front” of Cayman’s tourism growth and projections of future growth for Freig, highlighting the upcoming additions of room stock as a result of the anticipated completion of the Grand Hyatt Grand Cayman, the Hotel Curio Collection by Hilton Kailani Grand Cayman and One GT, as well as added room stock through Vrbo and Airbnb.

Harris said she sees it “a win” that fewer than two months after that presentation, American Airlines agreed to reintroduce the daily overnight flight, even if it is for a 26-day trial.

“I embrace any opportunity to show what we can do,” she said. “I’ll take the chance if there’s a benefit in the future.”

The additional evening flights are already available to book on aa.com.