Supersonic flow fields around Two-Stage-To-Orbit (TSTO) models with different configurations have been experimentally examined in this paper. Four configurations for the orbiter have been considered: A) a hemispherecylinder, B) a hemisphere-cylinder with a flat bottom, C) an obliquely truncated circular cylinder, and D) a cone-cylinder. All the flow fields around these models showed complicated shock/shock and shock/boundary-layer interactions, which can be categorized into three patterns, depending on the extent to which the separation shock wave contributes to these interactions. The models B, C and D were proposed to suppress the pressure rise due to the interactions observed in the model A. As a result, the model B showed almost the same interactions as the model A, while in the model C they did not present. In the model D, a large pressure rise was seen in the case with no clearance, whereas the model undergoes the least aerodynamic interaction at a rather large clearance. It is concluded from these results that the model C is less affected by aerodynamic interactions due to the clearance than the other models.