This paper investigates the aspects of regional digital convergence, i.e. the capability of the use of Information and Communication Technologies (ICTs) among all people living in the peripheral areas of a country, in relation to the ICT applications into the transport sector, known as Intelligent Transport Systems (ITS). It also examines the interdependent relationships between the digital and physical accessibility. Firstly, the ICT infrastructures and their access via the households and enterprises set the conditions for the use of ITS. On the other hand, the expansion of transport networks and decentralization of transport flows can contribute to the widespread adoption of ITS and ICTs in general, and the higher specialization and diversification of digital services. These interactions are analyzed in Greece, through investigating the spatial allocation of public expenditure, at a regional level, for the Information Society and the transport sector, during 2000–2009. The findings indicate that the increased concentration of public investments in road projects in peripheral areas does not imply the bridging of the digital gap between the metropolitan areas (Athens and Thessaloniki) and the rest of Greece. The need for designing a comprehensive regional investment policy is suggested to jointly reinforce the digital convergence and physical accessibility