On rough surfaces, two distinct wetting modes can appear. These two states are usually described by the theories of Cassie (drops suspended on top of roughness features) and Wenzel (drops impaled on roughness features). Whereas the wetting transition from the Cassie to the Wenzel state has been relatively well studied both experimentally and theoretically, the question of whether metastable Wenzel drops exist and how they transition to the Cassie state has remained open. In this work, we study the wetting behavior of microstructured post surfaces coated with a hydrophobic fluoropolymer. Through condensation, the formation of metastable Wenzel droplets is induced. We show that under certain conditions drops can transition from the Wenzel to the Cassie state.