In the past decade, I've identified 6 different species of Octopuses here in St. Croix; The Caribbean reef, brown-stripe, Atlantic long arm, The Caribbean two-spot, white-spotted and the common octopus. Here in St Croix, it is almost guaranteed to have an encounter on a night pier dive. They are elusive creatures that hind in a den and it's not uncommon to come across a nesting octopus, inhabiting an old bottle under the Frederiksted Pier.
There are no cuttlefish in the Caribbean. Period. The Caribbean reef squid is found throughout the Caribbean Sea as well as off the coast of Florida, typically in small schools of four to thirty and often observed near shore by divers and snorkelers. Reef squid are often confused with cuttlefish because they have large fins that wrap around their mantles. I have also observed and photographed the longfin squid in St. Croix.