A system and method for intelligently caching data based on predictable schedules of mobile transportation environments. For example, one embodiment of a system comprises: a plurality of mobile caches deployed within a corresponding plurality of transportation vessels/vehicles; a first mobile network interface coupled to each of the mobile caches; a plurality of edge caches of a content service provider, each of the plurality of edge caches to be filled from source caches in accordance with a cache fill policy; a stationary network interface coupled to each edge cache to automatically establish a high speed wireless connection with the first mobile network interface when a first vessel/vehicle arrives at the port, station, or terminal; and cache management logic to identify portions of multimedia content to be provided to a first mobile cache from a first edge cache upon establishment of the high speed wireless connection.