Diffusion in recent decades of Cannabis sativa L. varieties with low concentrations of tetrahydrocannabinol (THC) is leading to a specialization in the whole sector, requiring innovative techniques for input optimization according to the variety and the growing environment. The continuous agricultural evolution aims at increasing the sustainability of cultivation systems, pushing toward precision technologies application for inputs management. Cannabis monitoring can benefit from Unmanned Aerial Systems applications combined with image thresholding techniques for reliable and effective near-real-time plant detection and numbering. The work compares and evaluates the potential of two threshold segmentation techniques for Cannabis plant detection and counting in two experimental fields in Italy on a multitemporal scale, bringing such techniques in competition with machine learning for object detection. The Otsu segmentation technique demonstrated more reliable performances at the early stage of cultivation with an accuracy of 0.95. The Canopy Height Model technique showed increasing performances during the growing season. Future works will compare thresholding segmentation techniques with machine learning (ML) approaches and their potential as a supporting tool for ML image annotation.