Brother Marie-Victorin was the founder of the Montreal Botanical Garden, and one of the most important figures in the botanical history of Canada. Between 1938 and 1944, he undertook seven major plant exploration expeditions to Cuba that resulted in the discovery of several new Cuban endemics. Archival research carried out in the Division de la Gestion de Documents et des Archives (University of Montreal) revealed that during his voyages to Cuba, he made three major side-trips in 1940, 1941, and 1942 to other regions of the Caribbean. Specifically to Barranquilla (Colombia), Haiti, Jamaica, Puerto Rico, Trinidad, and Yucatan (Mexico). We could not find any of his written accounts of his 1940 voyage to the Yucatan; however, we were able to find a collection of photographic slides. An unpublished 33-page travelogue of his 1941 trip to Colombia, Jamaica, and Trinidad was discovered, studied, and translated into English, with annotations. Furthermore, we examined and interpreted two of his published papers that described the 1942 visits to Haiti and Puerto Rico. During these three “out-of-Cuba” voyages, no plant material was collected; however, Brother Marie-Victorin's written accounts and the 502 photos that he took provide unique insights into Caribbean society of the 1940s, as well as on the naturalists and botanists working in the region, and the plants and habitats they encountered. Brother Marie-Victorin's records highlight racial discrimination against those of African descent in Jamaica and Trinidad. It appears that these trips did not lead to major botanical research initiatives. Furthermore, the few collections that he made for potential propagation in botanic gardens or botanical institutes are not currently being grown any longer. The trips had clear leisure aims and they were centered on learning about the society, the flora, and plant science research activities of the visited areas.