Simple Summary: Over the last decades, visual endoscopy has become a gold standard for the detection and treatment of gastrointestinal cancers . However, mastering endoscopic procedures is complex and requires long hours of practice . In this context, simulation-based training represents a valuable opportunity for acquiring technical and cognitive skills, suiting the different trainees ’ learning pace and limiting the risks for the patients . In this regard, the present contribution aims to present a critical and comprehensive review of the current technology for gastrointestinal (GI) endoscopy training, including both commercial products and platforms at a research stage . Not limited to it, the recent revolution played by the technological advancements in the fields of robotics, artificial intelligence, virtual/augmented reality, and computational tools on simulation-based learning is documented and discussed . Finally, considerations on the future trend of this application field are drawn, highlighting the impact of the most recent pandemic and the current demographic trends . Abstract: Gastrointestinal (GI) endoscopy is the gold standard in the detection and treatment of early and advanced GI cancers . However, conventional endoscopic techniques are technically demanding and require visual-spatial skills and significant hands-on experience . GI endoscopy simulators represent a valid solution to allow doctors to practice in a pre-clinical scenario . From the first endoscopy mannequin, developed in 1969, several simulation platforms have been developed, ranging from purely mechanical systems to more complex mechatronic devices and animal-based models . Considering the recent advancement of technologies (e.g., artificial intelligence, augmented reality, robotics), simulation platforms can now reach high levels of realism, representing a valid and smart alternative to standard trainee/mentor learning programs . This is particularly true nowadays, when the current demographic trend and the most recent pandemic demand, more than ever, the ability to cope with many patients . This review offers a broad view of the technology available for GI endoscopy training, including platforms currently in the market and the relevant advancements in this research and application field . Additionally, new training needs and new emerging technologies are discussed to understand where medical education is heading.