Instrumented exploratory drilling in rock has been widely used in geotechnical engineering and in the oil and gas industry to characterize geological formations and to investigate the presence of subsurface cavities and soft spots. Instrumented drilling involves monitoring the drilling process by measuring a number of drilling parameters using sensors that are mounted to the drill rig. The data collection process used in conventional instrumented borehole drilling suffers from several limitations that are associated with the use of cables. The cables are susceptible to damage during drilling and could cause disruption to the drilling process. The objective of this paper is to present an enhanced system for instrumented borehole drilling that was developed to achieve (1) wireless data acquisition that would eliminate the need for cables and allow for remote access and control of the data, (2) automated real-time detection of cavities and soft spots, and (3) enhanced measurement of the rate of penetration using a laser sensor. Field implementation and testing of the wireless drilling system indicated an adequate functionality of the sensors used and their proper communication with the wireless data acquisition system and offered a realistic demonstration of the system.