The aim of this paper is to critically analyze Kolb’s theoretical model on experiential learning from a constructivist perspective by relating it to more contemporary practices in the field of experiential education. It has been observed that the experiential learning phenomenon has been overwhelmed by individualistic views and overly deterministic intents of reconceptualization. In particular, this paper investigates the deficiencies in Kolb’s experiential learning cycle by comparing it with alternate conceptions to learning proposed by Fenwick (2001). The discussion further develops a theoretical critique based on assumptions compiled after a theoretical discourse of the literature enlisting factors which question the effectiveness of the learning cycle. Lastly, the authors propose modifications in the concept of experiential learning by identifying the environmental and structural constraints which may affect the effectiveness of the experiential learning process.