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"Whipple the Happy Dragon" is the second part of the Adventure Time miniseries Islands and the twenty-first episode in the eighth season of Adventure Time. It is the two hundred and forty-sixth episode overall.
Finn, Jake, and Susan set sail on a ocean voyage full of wonders and danger. 
The episode begins with a shot of Susan manning the helm on the H.M.S Sugar Spit. The scene changes to Finn inspecting a map of Ooo, however Finn does not know how to navigate, which Jake points out. Jake reveals that he knows how to navigate without computers, using a sextant and mental math to plot the path they need to take to get to the islands. Finn notifies Susan that they have a set course, and they then all go to the deck celebrating. As Finn observes his surroundings, watching dolphins jump around the sailboat, he hears a group of Elephants singing a summons. Finn uses his telescope to get a better look, and witnesses an Ele-fly emerging from a volcano. Finn follows the Ele-fly with his telescope which leads him to a dragon running from Pirates. The rationale for hunting the dragon appears to be that they dislike him and he makes them uncomfortable. As Finn sails to the dragon's direction Susan disagrees with Finn, on the account that the dragon could be much needed food. Meanwhile during the discussion, the dragon creates a whirlpool destroying the pirate's ship. The pirates accept the consequence to their actions and flee on life boats.
The dragon is heard calling the crew, making his way over and greeting them. The dragon's name is Whipple, and he apologizes for inconveniencing them. The crew and Whipple become acquainted with each other, and Whipple steers them in their desired direction after Jake informs everyone he lost his sextant.
The crew appears to be bored and irritable after listening to Whipple's ideas for some time. Finn takes out a notebook, sketching earplugs, and passes the drawing to Susan, who passes it to Jake. Jake evidently understood what Finn requested, and stretched earplugs for both Susan and Finn. Meanwhile BMO, who watched Jake form earbuds for Finn and Susan, busts out of the hold begging to have earbuds, too. Due to BMO's outburst, Whipple learns that the crew did not want to hear him, so in anger, he destroys their boat launching them into the air.
Jake stretches into a raft catching everyone from falling into the ocean, and then decides to form a sailboat. BMO uses a navigation app to find a course due to Jake being unable to determine where to go. Jake steers away from the course going after what appears to be Margaret and Joshua, asking for help. It is immediately revealed that Jake is hallucinating, and they are headed towards sea weed. BMO alerts the crew that they are headed to Poison Reef, so Finn and Susan try to use the boom to prevent them from reaching it. Unfortunately, doing so moves them away from what Jake sees as Joshua and Margaret, causing Jake to fight back. Jake knocks Finn off of the boom and into ocean, revealing to Finn a horde of poisonous jellyfish under Jake. Susan pulls Finn out of the water, and Finn informs Susan that Jake is hallucinating due to the poisonous jellyfish. Susan and Finn dive into the ocean and punch the jellyfish off of Jake. As they resurface, Susan finds a small child on the deck, but the hallucination goes away after Finn pulls off a jellyfish from Susan's head.
Finn tries to boost the morale in the crew dismissing the unfortunate turn of events as "minor setbacks," but Jake ignores him, and says that he is ready to leave. After being questioned on the importance of the trip to Finn, he opens up telling them that he does not want to remain ignorant on the whereabouts of his species; he needs closure.
Whipple suddenly emerges from the ocean, letting Finn know that he understands how he feels, and apologizes for destroying their boat earlier. Finn apologizes for hurting his feelings, although he is unsure of what he should be apologizing for. Whipple warns the crew that the path that they are taking is very dangerous. After they admit that they are ready, Whipple also warns them of the Islands' colossus, and blows "a mighty wind," taking them over the dangers they would have faced in the Sea of Sure Death. They land near a cloud of fog, and inside of the fog lie broken ships. The episode ends with the colossus resurfacing in front of the crew, grabbing and then dropping them into the ocean.
- Joshua (hallucination)
- Margaret (hallucination)
- Poisonous Jellyfish
- Frieda (hallucination)
- Princess Bubblegum (pictured)
- This episode is the last time where Susan speaks in broken English.
- Whipple mentions a character named "Squirrel Girl," most likely a reference to the superhero from Marvel comics.
- The particular way Jake stretches himself to form a hammock bears a high resemblance to how Spider Man shoots his web.
- Susan sees a hallucination of Frieda, who is revealed later in the episode "Hide and Seek."
- Finn mentions his former fear of the ocean. He discovered this fear in the season 1 episode, "Ocean of Fear" and conquered it in the season 5 finale, "Billy's Bucket List."
- Finn mentions his parents finding him on a boom boom leaf. This was revealed in "Memories of Boom Boom Mountain."
- This episode was released for digital download and DVD on January 24, 2017.