Ground-penetrating radar has emerged as a prominent non-destructive evaluation tool for the study of inaccessible subsurface elements of cultural heritage structures. Often of central interest is the desire to image the remains of a pre-existing historic structure that is located directly beneath a more recently built one. The interpretation of GPR images in such cases is usually difficult due to ambiguities caused by the presence of pervasive clutter, environmental noise, and overlapping target signatures. Sites with abundant ground truth allow for more confident interpretations and serve as a useful testbed to assist similar studies at other places, where little or no ground truth is available. This study reports GPR interpretations of structures belonging to the 19th century Citadel beneath the main prison cellhouse at Alcatraz. At this site, lidar scans, direct observations, and historical documents are available to facilitate identification of radar target signatures. A general interpretation of the acquired radargrams is made in this paper, while the companion paper presents more advanced analysis of target signatures based on curvelet image processing. This study points to the development of a radar facies classification scheme that is specific to cultural heritage investigations.