The crew meets with the Grandberry Pirates after their victory. Chip slowly learns what it really means to be a pirate. Jay discovers the terrifying truth of the Navy. Gillion gets even moister and learns a new spell.

Chibo & Chums face off against the Grandberry Pirates! Will Chip be able to best Captain Lizzy? Will Gillion's moisture levels be enough to best Caspian? WILL JAY'S GRANDMOTHER FINALLY DIE?

The crew is running out of time to secure victory in The Paramount Tournament! With only a few teams left, will they be able to JACK THE JOLLY ROGER?? Gillion offers a challenge to a worthy foe. Jay's grandmother unleashes her elderly power. Chip has so many pants. Pretzel fulfills her destiny.

The all-out pirate brawl begins at the Paramount Tournament! Will the crew be able to best the other teams at this game of skill and wit? Find out in- wait they're all just killing each other instead. wait. hang on. oh no.

The crew takes a brief respite in a unique Tavern. Jay takes a bath. Chip becomes a Viking. Gillion leaves a bad review.

Can you believe it? The crew arrives on an island and the FIRST thing they do is pants some dudes!

The crew faces off against their first sea-faring enemies, and they're out for blood.

Gillion and the Tidestriders perform their first-ever single and rock the Island. Gillion steals someone's heart. Jay and Chip scam idiots.

The crew faces off against Malice, The Empress of the Isle, in one final encore.

The crew reaches the peak of Desire Island, and begin to unravel their own mysteries. Jay finds a book belonging to someone fishy. Gillion makes everything go downhill fast. Chip has a plan.