Cayman Airways (the local airline where I live) has announced its plan to modernize its fleet. Currently the main fleet (discluding Cayman Airways Express) has 4 737-300 aircraft. Cayman Airways plans to lease 737-800s to replace them by the end of 2016. In 2018 to 2020 4 737-8MAX aircraft will be delivered and will make Cayman Airways have the most modern fleet in the carribean region.
Here is the link to the article: https://www.caymanairways.com/FleetModernizationPlan