No, you generally do not have to fold your stroller when boarding the Disney Skyliner gondolas at Walt Disney World. This is one of the biggest "quality of life" benefits for parents compared to Disney buses or parking lot trams. As long as your stroller is a single or a tandem double (front-to-back) and fits within the standard cabin dimensions, you can simply wheel it straight onto the gondola while your child remains seated. However, side-by-side double strollers are the exception; due to the width of the doors and the interior bench configuration, these must be folded before you board. Additionally, if the gondola is exceptionally crowded or if you are asked by a Cast Member for operational reasons, you may need to fold it. For 2026 visitors, it is worth noting that "stroller wagons" are still strictly prohibited throughout Disney parks and transport, including the Skyliner, unless they are officially tagged as a medical necessity.