The skill of spatial learning and orientation is fundamental in humans and differs widely among individuals. Despite its importance, however, the malleability of this skill through practice has scarcely been studied empirically, in contrast to psychometric spatial ability. Thus, this article examines the possibility of improving the accuracy of configurational understanding of the environment by training. A total of 40 adults with a poor sense of direction participated in the experiment; and were randomly assigned to either a condition in which they received feedback only or a condition in which they additionally practiced allocentric spatial updating. Participants walked one route in each session, once a week for 6 weeks, and conducted spatial tasks designed to assess their knowledge of the route. A total of 20 people with an average sense of direction also participated as a comparison group. Results showed that training in allocentric spatial updating improved the accuracy of direction estimates, although the size of the effect was limited: the improvement was not large enough to equate the performance in the groups with a poor versus average sense of direction. The two groups, however, did not differ in spatial skill in mental rotation or path integration. Feedback was effective for improving accuracy in straight-line distance estimates and sketch maps: repeated trials with feedback led to improved accuracy by the sixth session to a level comparable to the group with an average sense of direction. The results show that flexible translation between viewer-centered and environment-centered representations is difficult and not readily trainable, and provide insights into the nature of individual differences in large-scale environmental cognition.