An apparatus includes an initial planning module, a tandem implementation module, and a scheduler module. The initial planning module is structured to interpret one or more fleet delivery requirements, assets, drivers, and vehicle descriptions. The tandem implementation module is structured to determine a travel schedule with respect to a first vehicle and a second vehicle that enables the first vehicle and the second vehicle to travel in tandem for a least a portion of a route in response to input from the initial planning module. The scheduler module is structured to provide a fleet delivery schedule to the first vehicle and the second vehicle in response to the determination of the tandem implementation module.