Mysteriousuniverse.org describes various sightings of pterosaurs in Cuba, stating, "...Californian woman by the name of Patty Carson reported seeing something both inexplicable and frightening in the skies above Guantanamo Bay when she was a little girl living there at the naval base. In 1965, Carson was walking home one day with her little brother when they noticed something large rummaging through tall grass by the side of the road. She recounted how a featherless, winged creature that was as tall as a man and possessed a plenitude of small, needle-like teeth, as well as a long tail with a tip shaped like a diamond, suddenly popped its head and shoulders up over the top of
the grass. She described it as a “flying dinosaur,” and said that it was very close, only about 30 feet away...In 1966, only a year after this incident, Patty’s brother Tom Carson would have another separate sighting of the same beast. This time, the boy, who was 10 years old at the time, saw the creature when he was by himself. Although he only glimpsed it for a few seconds, Tom remembered that it had a tail that resembled 'the shaved tail of a dog.'
At this point, one could be forgiven for questioning the reliability and veracity of these particular reports, but they becomes more intriguing when compared to another eyewitness account that occurred in the same area just a few years later in 1971. A U.S. marine by the name of Eskin Kuhn, who was stationed at the base
in 1971, reported seeing what he described as two 'pterodactyls' one day while taking a break outside of the barracks."
According to knowablenews.com, a lady who was on a cruise in the Caribbean saw two pterosaur like creatures.