The Mediterranean is an inhabited space made up of historical and cultural flows. It is also a vulnerable ecosystem seriously affected by anthropic and environmental pressure. Mass tourism, the serious distress and growing abandonment of coastlands and islands, and the increasing extreme natural events cause a progressive vulnerability and loss of identity that force the Mediterranean living space into a constant emergency. To this aim, Italian policies on climate change adaptation as the National Plan for Adaptation to Climate Change (PNACC) and the National Strategy for Sustainable Development (SNSvS), in coherence with the International framework defined by the 17 SDGs of the Agenda 2030, the New Urban Agenda, the European Green Deal and the Biodiversity Strategy for 2030 aim to identify new ecological adaptation strategies, based on the morphological and environmental reconnection and reconfiguration of the existing cultural and natural values. A new integrated and trans-scalar approach is essential to promote sustainable use of cultural resources and a comprehensive, ambitious, and long-term planning strategy to protect nature and local communities, reversing the degradation of ecosystems and landscapes. In this framework, small islands represent an essential device to experiment and design new ecological and adaptive projects capable of building a new sense of social cohesion and an efficient awareness of natural and heritage resources, leading to a sustainable, more inclusive, and equitable concept of communities. In particular, the Pontine Archipelago in the Tyrrhenian Sea well represents the insular dimension in which to experiment with strategies, tools, and projects for ecological adaptation to risks, promoting a new balance between conservation, sustainable use, and equitable sharing of natural and cultural resources.