Driver behavior and visual perception are very important factors in the management of traffic accident risk at tunnel entrances. This study was undertaken to analyze the differences in driving behavior and visual perception at the entrances of three types of tunnels, namely, short, medium-length, and long tunnels, under naturalistic driving conditions. Using three driving behavior indicators (speed, deceleration, and position) and two visual perception indicators (fixation and saccade), the driving performance of twenty drivers at six tunnels (two tunnels per condition) was comparatively analyzed. The results revealed that the speed maintained by the drivers prior to deceleration with braking under the short-tunnel condition was significantly larger than that under the medium- and long-tunnel conditions and that the drivers had a greater average and maximum deceleration rates under the short-tunnel condition. A similar general variation of driver visual perception appeared under the respective tunnel conditions, with the number of fixations gradually increasing and the maximum saccade amplitude gradually decreasing as the drivers approached the tunnel portal. However, the variation occurred approximately 60 m earlier under the short-tunnel condition than under the medium- and long-tunnel conditions. Interactive correlations between driving behavior and visual perception under the three conditions were established. The commencement of active deceleration was significantly associated (with correlation factors of 0.80, 0.77, and 0.79 under short-, medium-, and long-tunnel conditions, respectively) with the point at which the driver saccade amplitude fell below 10 degrees for more than 3 s. The results of this study add to the sum of knowledge of differential driver performance at the entrances of tunnels of different lengths.