Not a book or a story but I would HIGHLY recommend a visit to the maritime history museum in Sevilla, Spain. Tonnes of very entertaining interactive resources there about naval history in the early new world.

EDIT: My favourite story from there was that of a ship that was blown way off course and ended up landing in a fairly uninhabited area far south of the intended destination. While most of the crew were of the lower classes, one of the paying passengers was a very well to do lady of the higher classes. After a period of being stranded and clothing starting to shred, the higher class woman decided she could not let the lower class men see her naked, so she demanded they dig her a hole in the ground which she stayed in while the party continued to look for help.

Unfortunately I don't remember any more details (especially as to if she was saved or not), if anyone can point me to an online resource that covers this that would be amazing.