Hammerhead launcher configurations, characterized by a larger diameter in the payload fairing than the rest of the launch vehicle, face substantial challenges during transonic operations due to their susceptibility to flow separation. This experimental study investigates the influence of the nose and boat tail geometry on the flow around hammerhead configurations in the transonic regime (Ma = 0.7–0.8) and for various angles of attack (α = 0–4°). To gain a general understanding of the shockwave structures, flow separation and reattachment, oil flow and schlieren visualizations were employed. Schlieren visualizations were also utilized to characterize the level of unsteadiness in these regions. Additionally, particle image velocimetry was employed to quantify variations in the velocity field. The study’s findings reveal an optimization of flow performance in the presence of a bi-conic nose, attributed to the creation of two-shockwave structures with relatively low intensity. This is in contrast to the ogive and conic noses, which exhibit a single, more detrimental shockwave structure. The investigation into different boat tail angles indicates that adopting low-angle boat tails (5° and 15° compared to 34°) leads to a noticeable reduction in the separated area, albeit associated with an increase in the range of oscillation of the shockwave structures.