Guided by insights on the mapping class group of a surface, we give experimental evidence that the upper bound recently proven on the diameter of the flip graph of a surface by Despré, Schlenker, and Teillaud (SoCG'20) is largely overestimated. To obtain this result, we propose a set of techniques allowing us to actually perform experiments. We solve arithmetic issues by proving a density result on rationally described genus two hyperbolic surfaces, and we rely on a description of surfaces allowing us to propose a data structure on which flips can be efficiently implemented