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 cities in the area, like Havana and Kingston.
In 1673, Thom Kavanagh , a native from Boston who worked in the Peter Beckford's estate in Jamaica, was search by the Grand Master Templar Laureano Torres y Ayala. In fact Thom was a Sage, a reincarnation of Aita, who knew the location of the Observatory where was hidden a powerfull device. The Assassins, with Bahlam, decided to save Thom before the Templars captured him and lead him to Tulum. After the events, Thom Kavanagh didn't wanted share the location of the Observatory to the Assassin before he could explain his visions. Bahlam accepted and Thom left Tulum with the help of Bahlam's son, Ah Tabai. Thom never returned in Tulum.
Four decades later, Ah Tabai became the Mentor of Caribbean Assassins and was targeted by Laureano Torres, who asked to the former british Assassin, Duncan Walpole, to kill him. Duncan traveled to west indiesa also to sold a map which indicated the location of the Assassins in the area and a blood vial to the Templar. But in june 1715, near Cape Bonavista Ducan was attacked by a pirate's ship and killed by the pirate Edward Kenway, who decided to impersonating Duncan to collect the reward.