Practice points• The availability of active new drugs has changed the natural history of advanced castration-resistant prostate cancer, significantly improving overall survival and thus leading to an increased risk of observing metastases in atypical sites. • Bone and lymph nodes are usually the most frequent sites for distant metastases arising from prostate cancer. Visceral metastases are rare and when they occur, they usually involve the liver and lungs. • The gastrointestinal (GI) tract is usually directly invaded from adjacent organs or enlarged lymph nodes. Hematogenous or lymphatic spread from prostate cancer to GI tube is uncommon, but the incidence seems to be increasing. • The presenting symptoms of GI metastases, such as nausea, vomiting and abdominal pain and body weight loss are usually nonspecific, and all of them are often related to anticancer treatments or progressive disease. • In patients with a history of prostate cancer and new-onset GI symptoms, GI metastases should be considered in the differential diagnosis.The introduction of docetaxel into clinical practice and the more recent availability of other active therapeutic options, such as cabazitaxel, abiraterone acetate, enzalutamide and radium-223, have significantly improved the clinical outcomes of patients affected by castration-resistant prostate cancer (CRPC). Bone and nodes metastases are usually the first presentation of advanced disease, but the improvement in overall survival and the greater use of imaging techniques for restaging of metastatic CRPC patients have led to a previously unexpected clinical scenario characterized by an increased incidence of visceral metastases not only in the liver and lungs, but also in atypical sites such as the brain or gastrointestinal tract. We describe a rare case of CRPC metastasizing to the small bowel with particular endoscopic and radiographic findings.