In this paper, we present a brief evolutionary approach to wooden boat architecture, arguing against current misconceptions that such vessels are environmentally unsustainable and just objects of beauty. The proposition is that wooden boats evolve through time and that the combination of the fundamental elements of wooden sailing boats with new technologies for energy efficiency can ensure their sustainable future. Our claim is that wooden boats in Greece provide a low-carbon energy efficient solution to the European and International sustainability agenda. With small modifications, without changing drastically the boat shapes or typologies, wooden sailing boats can be optimized to navigate using renewable energy (e.g., by using wind energy and flexible solar panels on sails as well as electric propulsion). Mathematics, hydrodynamics, naval architecture, and marine engineering are only a few fields that come together to support this powerful synergy aiming for a smart sustainable future of seafaring.