In 1503, Ezio Auditore da Firenze sent a group of Assassins to Constantinople, where they managed to retrieve maps of the New World from Piri Reis' workshop. Realizing that the Templars were already expanding their influence to the new-found lands, the Assassins swiftly followed suit. After these Assassin immigrants from Europe made contact with the indigenous peoples in the Caribbean, a lot of natives joined the Order, finding similarities between their own way of living and the Assassin ideology.
By 1510, the Caribbean Assassins were known to be located in Florida, where they discovered and protected the Fountain of Youth, which held an Apple of Eden. That year, the Assassins welcomed the former slave and translator for the Spanish Army, Alonso Carlo, and his adopted son Miguel Ramon Carlo de Lugo, who they trained to become an Assassin, after their escape from persecution by Juan Ponce de León. In 1521, Ponce de León arrived in Florida searching for the Fountain of Youth, where he was halted by Miguel. After Ponce de León refused to stop his search, the Assassins shot him with poisoned arrows, which later caused his death.
During the 18th century, Caribbean Assassins had the same organization of the Levantine Assassins, with their Head Quarter located in Tulum and some Bureau in the most important city in the area like Havana and Kingston.