Arsenic (As) is one of the most common inorganic pollutants; unfortunately, it is also one of the most toxic and is therefore a cause of great concern for the health risks that could result from it. Removing arsenic from the soil using phytoremediation approaches is an effective strategy, and several studies demonstrate the ability of Cannabis sativa (TSN 19109, hemp) to tolerate this harmful contaminant. The aim of this work was to identify the best experimental conditions for a phytoremediation plan to be applied in a disused area located in Sicily (Italy) and contaminated by As, comparing Cannabis sativa with Brassica juncea (TSN 23059) and Zea mays (TSN 42269, corn). To assist the process, several chelating agents were tested to improve arsenic mobility, and two different sets of arsenic-tolerant bacteria were isolated from the rhizospheric soil of indigenous herbaceous species and used to promote plant growth, leading to a significant improvement in terms of biomass produced and phytoextraction. After the combined treatment, the arsenic content in the aerial part of the plants increased by more than two orders of magnitude (e.g., from 0.05 to 6.57 mg kg−1, from 0.04 to 6.69 mg kg−1, and from 0.03 to 5.57 mg kg−1 for brassica, corn, and hemp, respectively), confirming the marked increase in the total absorption of As by plants.