(1) Background: Many professional and recreational cyclists experience that neck extension in time trial position negatively impacts either speed, comfort, or power production—especially at high cycling speeds or for long distances. We conducted a feasibility study with one subject to assess whether redirecting the sight of a cyclist while in time trial position could reduce aerodynamic drag and neck strain by maintaining a more neutral neck position. (2) Methods: A physical immersive exercise bike was developed (called a FAAST-trainer) that emulates posture, velocity, and power to be delivered by the user through an adaptable power load adjusted in real time. As an optical intervention, we used prism glasses to redirect the cyclist’s sight. The subject trained his perceptive-muscular system while cycling on the FAAST-trainer to get used to wearing prism glasses. He feels confident that the glasses are safe to test for future experiments in a velodrome. (3) Results: A consistent reduction in drag was found (p < 001) when wearing prism glasses with the FAAST-trainer, ranging from 3.5% to 4.7%. Accordingly, the cyclist could thus save between 9.7 watts and 13.0 watts cycling at 45 km/h, compared to having his head in an upright position. (4) Conclusions: Our experiment on the FAAST-trainer indicates that an optical intervention to reduce neck extension by redirecting sight might be safe to use for outdoor cycling. However, no vestibular effects, neither auditive nor complex combinations, were assessed, so we recommend additional research and development of a dedicated design for the prism glasses. Outdoor experiments should be conducted to confirm this reduction in aerodynamic drag and further asses the safety when wearing prism glasses.