Transport Demand Management (TDM) is crucial in shaping travel behavior and enhancing urban mobility by promoting sustainable transport options. This study represents a comprehensive analysis of employee commuting behavior across seventy-seven cities in Italy, with a focus on Rome as a case study. It investigates some requirements of the workplace travel plan as a TDM strategy for promoting sustainable commuting. An online survey conducted in June 2022 yielded 2314 valid responses, including 1320 from private car drivers. K-means clustering was used to identify distinct behavioral patterns among commuters, revealing four clusters based on demographic factors and transport preferences, such as age, gender, family circumstances, vehicle ownership, willingness to walk, ride bicycles, or e-scooters, and reasons for mode choice. This study analyzed Rome’s public transport network, land use, and private car use. Results underscore the need for tailored transport policies that enhance inclusivity and accessibility, especially for employees with family members who cannot commute independently. A spatial analysis of Rome reveals significant infrastructure deficiencies, such as complicated transfers and inaccessible stations, which discourage PT use. Future research should explore the impact of remote work and psychological factors and conduct in-depth subgroup analyses to inform inclusive transport policy development.