In recent years, agencies around the world have invested huge amounts of effort toward digitizing many aspects of the world’s cultural heritage. Of particular importance is the digitization of outdoor archaeological sites. In the spirit of valorization of this digital information, many groups have developed virtual or augmented reality (AR) computer applications themed around a particular archaeological object. The problem of pose tracking in outdoor AR applications is addressed. Different positional systems are analyzed, resulting in the selection of a monocular camera-based user tracker. The limitations that challenge this technique from map generation, scale, anchoring, to lighting conditions are analyzed and systematically addressed. Finally, as a case study, our pose tracking system is implemented within an AR experience in the Byblos Roman theater in Lebanon.