Multi-level geometrical approaches in the study of aorto-coronaric bypass anastomoses configurations are discussed. The theory of optimal control based on adjoint formulation is applied in order to optimize the shape of the incoming branch of the bypass (the toe) into the coronary. At this level, two possible options are available in shape design: one implements local boundary variations in computational domain, the other, based on the theory of small perturbations, makes use of a linearized design in a reference domain. At a coarser level, reduced basis methodologies based on parametrized partial differential equations are developed to provide (a) a sensitivity analysis for geometrical quantities of interest in bypass configurations and (b) rapid and reliable prediction of integral functional outputs. The aim is (i) to provide design indications for arterial surgery in the perspective of future development for prosthetic bypasses, (ii) to develop multi-level numerical methods for optimization and shape design by optimal control, and (iii) to provide input-output relationship led by models with lower complexity and computational costs. We have numerically investigated a reduced model based on Stokes equations and a vorticity cost functional (to be minimized) in the down-field zone of bypass: a Taylor like patch has been found. A feedback procedure with Navier-Stokes fluid model is proposed based on the analysis of wall shear stress-related indexes