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The Spain–Portugal Cross-Border Cooperation Program launched the “Espomar” project in 2017, with the aim of designing a sustainable and transboundary maritime transport system in the Gulf of Cádiz, which includes the Spanish provinces of Cádiz (its Atlantic coast) and Huelva, together with the Portuguese region of the Algarve. This chapter limits the scope to the Algarve-Huelva connection and the resident population demand. The findings suggest a maritime connection defined and marketed as part of leisure activities. The demand for potential tourism packages created around boat trips appears to be promising. The sun beach, gastronomy wine and culture landscape vectors are the main attractors.