The maritime connections are vital to success of islands. Estonia has 19 permanently habited islands with at least five inhabitants. 16 of those are considered as small islands with an area below 100 km2. Their sea connections are secured (i.e. organized, financed) by the government or municipality. These small islands are very diverse -in terms of population, economic activity, infrastructure capacity and needs, etc. In this study, we have analyzed ten connections to seven Estonian small islands based on seven criteria. The criteria are as follows: passenger and vehicle volumes, frequency, reliability, speed and time, vessel suitability, harbours and transport access to the harbours from the landside. Thereafter, we have classified the connections to islands to four levels: (i) daily, (ii) scheduled, (iii) invitation-only and (iv) tourism. Finally, we raised several actions to improve the connections based on the defined service levels. This article addresses the problem of small island communities, the criteria that influence service, proposes service levels and scenarios and the tools for decision-makers to better organise the connections to island communities and to serve local residents and business as well as tourism.