The asphalt pavement is prone to temperature segregation. Most current studies focus on the temperature variation of hot-mix asphalt (HMA) during the paving stage in normal conditions. However, there is a lack of investigation on the performance of HMA during transportation process in winter. Insulation layers are necessary to prevent the change of HMA property, being equipped on the transportation truck. Field tests are performed on a highway to estimate the feasibility of insulation materials by monitoring the temperature variation of HMA throughout the transportation process. A Multiphysics finite element model is developed in COMSOL. The sensitivity analysis is conducted in terms of the properties of HMA. The insulation layer is effective in impeding heat transfer and keep the temperature of HMA. This improvement is more intense at larger depths. The environmental condition is less influential than the HMA properties. Recommendations are provided to moderate driving routes and locations of the mixing station by determining the worst cooling rate. This study aims to reveal the performance of insulation material and HMA in winter constructions for a typical highway. A theoretical basis is provided to optimize the construction sequences based on the investigation of the heat transfer mechanism.