Our aim was to understand how musculoskeletal training is structured in Italian residency programmes and the needs of young trainees. We sent out an online questionnaire (17 questions) to Italian Society of Radiology residents and board-certified radiologists aged up to 39 years. A total of 1144 out of 4210 (27.2%) members participated in the survey; 64.7% were residents and 35.3% were board-certified radiologists. Just 26.6% of participants had dedicated rotations for musculoskeletal training during their residency, although this percentage substantially increased in replies from northern Italy. One-fourth of residents had a scheduled period of musculoskeletal ultrasound. Most participants (76.3%) had <20 h per year of musculoskeletal lessons. The majority considered their musculoskeletal education poor (57.7%) or average (21.9%). According to 84.8% of replies, no dedicated training period about interventional musculoskeletal procedures was scheduled. Further, just 12.8% of residents took active part in such interventions. Nearly all participants believed that the musculoskeletal programme during residency needs to be improved, particularly concerning practices in ultrasound (92.8%), MRI cases interpretation/reporting (78.9%), and practice in ultrasound-guided interventional procedures (64.3%). Despite some differences in the structure of musculoskeletal education provided by different regions, there is a shared demand for improvement in musculoskeletal training.