The possibility to move independently outdoor has a huge impact on the quality of life. However, it requires complex skills, difficult to acquire for youth with intellectual disabilities (ID). They need an engaging and varied environment in which they can safely train these skills for all the time they may need. We present an exploratory study that aims to evaluate the usability of virtual reality (immersive headset) as learning tool for youth with ID. We developed a simulator of a pedestrian crossing able to reproduce different environmental conditions (i.e., weather, day-time/night-time, and drivers’ kindness). We tested our simulator with 15 people (9–18 years old) with ID. The tests showed good acceptability and a learning effect was visible after only four consecutive sessions, for a total of sixteen simulated crossings. However, additional studies are required (i) to assess in which measure this effect is imputable to actually learned crossing road skills or to a better control over the tool, (ii) to measure the transfer of the learning from virtual reality to real word conditions.