Here we explored the potential of two (ꟷ)-α-pinene-derived diols (PDOs) as building blocks to generate polyesters that mimic the properties of aromatic fossil-based polymers when combined with renewable diesters. The semi-crystalline or amorphous nature of the resulting polymers is tunable with the appropriate choice of diester. We demonstrate a concise synthesis of two novel unsymmetrical chiral PDOs on 20-40 g scale, together with eight structurally differing polyesters with excellent thermal stability; as reflected by high melting (270 o C, 277 o C), and glass transition temperatures (90 o C, 121 o C) for two of the polymers. The steric hindrance of the intact bicyclic αpinene ring structure protruding from the backbone of the polymers can also aid in the degradation process, manifested by facile chemical recycling of these polyesters under mild conditions to recover both monomers. Finally, our results show how the generated rigid polymers are prone to enzymatic degradation by PETase and cutinase without any chemical pre-treatment. Our results illuminate the potential of expanding the currently available chemical space in bio-based monomers to bicyclic diols to generate biomaterials with tailormade properties.