Small islands are recognized for their vulnerability to climate change. In this context, mitigation and adaptation policies are needed, but the ecological transition must be based on data. This study aims to assess the level of sustainability reached by 26 of the inhabited Italian small islands; it collects and analyzes the data and initiatives on the energy, mobility, waste, and water sectors and discusses the islands’ steps toward sustainability. The findings show that 18 of the 26 islands are not interconnected with the national grid and that the renewable sources cover less than 5% of the energy demand on 25 of the 26 islands. The number per capita of private vehicles reaches 90 cars per 100 inhabitants on three islands. The average of the separate collection of waste on the islands is 52%, which is far from the minimum recommended threshold of 65%. Pipelines or tankers on 17 of the 26 islands guarantee the water supply, and desalination plants are still not the rule, while the presence of wastewater treatment has been detected on 12 islands, and it often provides only partial treatment. An ambitious multi-stakeholder sustainability plan for each island should be developed to overcome the typical barriers of the island and to increase the building capacity in order to use economic incentives for that goal.