Through an urban tunnel-driving experiment, this paper studies the changing trend of drivers’ visual characteristics in tunnels. A Tobii Pro Glasses 2 wearable eye tracker was used to measure pupil diameter, scanning time, and fixation point distribution of the driver during driving. A two-step clustering algorithm and the data-fitting method were used to analyze the experimental data. The results show that the univariate clustering analysis of the pupil diameter change rate of drivers has poor discrimination because the pupil diameter change rate of drivers in the process of “dark adaptation” is larger, while the pupil diameter change rate of drivers in the process of “bright adaptation” is relatively smooth. The univariate and bivariate clustering results of drivers’ pupil diameters were all placed into three categories, with reasonable distribution and suitable differentiation. The clustering results accurately corresponded to different locations of the tunnel. The clustering method proposed in this paper can identify similar behaviors of drivers at different locations in the transition section at the tunnel entrance, the inner section, and the outer area of the tunnel. Through data-fitting of drivers’ visual characteristic parameters in different tunnels, it was found that a short tunnel, with a length of less than 1 km, has little influence on visual characteristics when the maximum pupil diameter is small, and the percentage of saccades is relatively low. An urban tunnel with a length between 1 and 2 km has a significant influence on visual characteristics. In this range, with the increase in tunnel length, the maximum pupil diameter increases significantly, and the percentage of saccades increases rapidly. When the tunnel length exceeds 2 km, the maximum pupil diameter does not continue to increase. The longer the urban tunnel, the more discrete the distribution of drivers’ gaze points. The research results should provide a scientific basis for the design of urban tunnel traffic safety facilities and traffic organization.