We devised an interactive environment in which subjects could perform simulated laparoscopic maneuvers, using either unconstrained movements or standard mechanical contact typical of a box-trainer. During training the virtual tool responded to the absolute position in space (Position-Based) or the orientation (Orientation-Based) of a hand-held sensor. Volunteers were further assigned to different sequences of target distances (Near-Far-Near or Far-Near-Far). Orientation-Based control produced much lower error and task times during training, which suggests that the motor system more easily accommodates tool use with degrees of freedom that match joint angles. When evaluated in constrained (physical box-trainer) conditions, each group exhibited improved performance from training. However, Position-Based training enabled greater reductions in movement error relative to Orientation-Based (mean −13.7%, CI:−27.1, −0.4). Furthermore, the Near-Far-Near schedule allowed a greater decrease in task time relative to the Far-Near-Far sequence (mean −13.5%, CI:−19.5, −7.5). Training at shallow insertion in virtual laparoscopy might promote more efficient movement strategies by emphasizing the curvature of tool motion. In addition, our findings suggest that an understanding of absolute tool position is critical to coping with mechanical interactions between the tool and trochar.