Quick Background: Raised in slipcove by father only who encouraged freedom and worship of Desna. Caleb dreamed of being a buccaneer all his life but Caleb's father admonished piracy and always maintained that honest work is its own reward. Caleb never agreed with this but respected his father so remained quiet. Meanwhile he visited temples of Desna and Cayden Cailean, learning about drink, travel and swordplay at night against his father's knowledge.
When he got older he discovered that his father was in fact a retired pirate himself! He had hidden this fact from Caleb in the hopes that his son wouldn't make the same mistakes he did. When Caleb found out, he ran away from home in order to fulfil his dream of being a famous pirate. He envisages it to be a wonderful, exciting life and has no idea about the horrors and hardships ahead of him.
Caleb is boisterous and loud but friendly at heart. On arrival at Port Peril, he immediately blew all his money on pirate gear (his starknife is the only thing he carries of any sentimental value) including clothes and tattoos (spent last 11gp on them so I assume decent quality) of Desna, Cayden Cailean and Besmara's symbols on his arms.
Caleb wears his hair in a loose ponytail and constantly has a cocky smirk across his face. He adopts an easy, low fencing stance during combat but is quick to dart forward to take advantage of openings or escape altogether through a larger foe's legs.