Role in the series
Crimson Castle first appeared in the episode "Hook and the Itty-Bitty Kitty" Captain Hook came to visit her but she had to run a few tasks and left her kitten, Rosie in the care of Hook and his crew. However, Rosie manages to flee from Captain Hook and his crew deep into Crimson Isle jungle. A few minutes later Jake and his crew were sailing by Crimson Isle and spotted the commotion from Hook and his crew and decided to come ashore to help.Mr. Smee explains to Jake and his crew what happen and the young pirate team offers to help Hook find Rosie.
Crimson Castle is visited again in the episode "A Bad Case of the Barnacles!" Jake and the crew had to find the Zebra Rose which would cure Bucky of a nasty case of Buccaneer Barnacles. But Captain Hook and Mr. Smee manage to steal the Zebra Rose believing that the puny pirate team were originally trying to locate the rose for Red Jessica.
In the episode "The Never Land Pirate Ball", When Red Jessica organizes a ball on Crimson Isle, Captain Hook was thrilled to be in the company of his beloved once more. But Hook can't seem to dance. Once on Crimson Isle Hook and his crew are greeted by Jake and his crew who were also invited. Hook smugly gloats that he'll be the one to win the rose in the Pirate Ball. However, Smee and the rest of the crew informs Jake that Hook still hasn't learned how to do the pirate waltz. Jake and his friends agree to teach Captain Hook how to perform a special dance in time for Red Jessica's Never Land Pirate Ball.
In the episode "Pirate Pals!" Captain Hook decides to visit his beloved Red Jessica with Mr. Smee much to Hook's surprise that he and Smee are not the only guest on Crimson Castle. Hook's thieving pirate rival Beatrice Le Beak has returned and she has her eyes on Red Jessica’s art collection.
In the episode "Mystery of the Missing Treasure!" Jake and his crew discover that someone has stolen their Team Treasure Chest. While searching for the suspect on Pirate Island Jake and his crew discover a perfume bottle and a feather Izzy determined the culprit was a female pirate so the young pirate sail to Crimson Isle ask Red Jessica if she knew who took the Treasure Chest. At Crimson Castle Red Jessica identified the fragrance as French Forever flowers but couldn't recall the feather but knew it looks familiar.
In the episode "Smee-erella!", Red Jessica's held her Pirate Convention at Crimson Castle with the assist of her new friend and future first mate Mollie assisting Red Jessica with the festivities.After being transformed into the dashing, swashbuckling "Buck Buccaneer" by Pip the Pirate Genie, Mr. Smee attends Red Jessica's Pirate Convention and befriends his idol First-Mate Mollie.Captain Hook soon becomes envies of Buck Buccaneer getting closer to Red Jessica and tries many attempts to foil Buck.
Crimson Castle makes a brief appearance in the episode "Dancing with Pirates ", Jake explains to the viewers that even dancing can be a useful pirate skill. Red Jessica is seen dancing with Captain Hook during the pirate waltz inside Crimson Castle ball room.