TRIP and TRAIL: What do you need to do during the 2025 Benefits Choice Period that ends on June 2, 2025? TRIP is the primary medical and prescription drug program for retirees who are not yet eligible for Medicare. In 2025, vision & dental will be included. TRAIL is the Medicare Advantage program for retirees who are Medicare eligible. We'll cover how and when retirees transition from TRIP to TRAIL, discuss enrolling if never enrolled in the program and re-enrollment in the program.