Regional development depends on the complex approach to the business environment, where the logistics system can either promote or restrict the economic development at the same time. Logistics and transport system can simultaneously be a promotional factor of the innovation in the regions and it can be itself the subject to technological and process innovation as well. The logistics system of the islands in Western Estonia is an integral business environment re-integrating institutions with particular functions into a coherent entity reacting flexibly to the changes on the market. The main goals of these entities is to ensure time and spatial profitability of the goods and to increase supplementary value and customer satisfaction. The interaction between the economic development and transportation is quite complex. Transportation improvements may result in the growth in the other sectors, ultimately leading to economic growth, but transportation improvements can also have a negative impact. The aim of the present article is to provide a survey of the regional economic considerations and accessibility factors, as well as an empirical case study involving specific Estonian islands. The transport connections between the island and the mainland play a significant role in the sustainable development of the economies on Saaremaa and Hiiumaa. In this paper I would also like to underline the importance of the role played by technology and the personnel.logistics system, transport connection, accessibility, mobility, interaction.