The Strait of Messina occupies a strategic position in the Mediterranean, representing an environmental and territorial peculiarity. The Strait Area is today at the center of the political debate for the stable crossing project, a strategic infrastructure work for Italy and Europe. With the Strait Bridge, territorial arrangements, sea fronts, infrastructure systems, and urban and architectural dimensions will change. It appears necessary to prepare the territories and take advantage of all the opportunities related to future scenarios. The Strait Area is not only marked by the crossing, but the whole territorial and urban system—the coastal strip and inland areas—becomes an active part of the processes of territorial regeneration and development.

Methods: The article, after an examination of the best practices and experiences of the world's Straits, analyzes useful case studies to understand what processes and phenomena “cross” them and what works, what urban, spatial, and architectural interactions and strategies they intercept or lap up. Marine “straits” are unique, and one realizes that the strength of their peculiarities lies not only in their function as a natural link between two shores but also in their role in channeling flows and energies.

The goal is to understand their extraordinary potential to promote a synergistic and sustainable transformation, devising strategies to prevent the opportunity of the construction of the Strait Bridge from becoming a missed opportunity for the enhancement of its shores as catalysts for rebirth and innovation. The paper addresses the relationship with the environment and design responses with respect to the intervention priorities that emerged from the case studies, proposing a regeneration model. Attempts are made to identify possible design strategies so that the bridge does not merely unite two shores but relates to socio-economic issues, regeneration, and architectural and urban enhancement, involving resources and actors in the Straits area.