If you only know Hiccup Horrendous Haddock III from the DreamWorks movies, you’re basically looking at a totally different person. Honestly. In the films, he’s a misunderstood teen genius who invents gadgets and flies a sleek, night-black dragon. But in the actual books—specifically How to Train Your Dragon Book 2, titled How to Be a Pirate—Hiccup is a scrawny kid who can barely get his tiny, selfish dragon to listen to a single word he says.
It’s messy. It’s loud. It involves a lot of mud.
Most people searching for info on the second book in Cressida Cowell's legendary series are looking for the plot or wondering if it follows the movie sequels. It doesn't. Not even a little bit. How to Be a Pirate is where the world of Berk actually starts to get dark and complicated, shifting from a simple story about "training" into a genuine saga about legacy, greed, and what it actually means to lead people who don't want to follow you.
The Weird, Gritty Reality of How to Train Your Dragon Book 2
In this installment, the Hooligan tribe isn't worried about Drago Bludvist or hidden dragon sanctuaries. They're worried about Swordfighting at Sea. This is a core part of the Viking curriculum, and Hiccup is, unsurprisingly, terrible at it. While the movie version of Hiccup has some "chosen one" vibes, the book version is constantly just trying to survive the sheer stupidity of his peers.
The plot kicks off when a massive storm unearths an old coffin. Inside isn’t just some random Viking, but a man claiming to be the heir to a massive pirate treasure. This is Alvin the Treacherous. If you’ve seen the TV shows like Dragons: Riders of Berk, you know the name, but the book version is far more sinister because he’s a master of disguise and psychological manipulation.
He tricks the Hooligans into a treasure hunt for the lost hoard of Grimbeard the Ghastly. This is where Cowell’s writing really shines. She builds this mythos of Grimbeard—Hiccup’s great-great-grandfather—who was essentially the most terrifying pirate to ever sail the Inner Seas. The treasure hunt isn't some fun Goonies adventure. It’s a death trap.
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Toothless is Kind of a Jerk (And That’s Why He’s Great)
We have to talk about Toothless. In How to Train Your Dragon Book 2, he isn't a majestic Night Fury. He’s a Common or Garden Dragon. He’s about the size of a pug, he has no teeth (hence the name), and he is incredibly lazy.
The relationship here is the heart of the book. Hiccup has to "train" him through negotiation and bribes rather than through some mystical soul-bond. It’s more like trying to convince a toddler to eat broccoli than it is training a loyal pet. In How to Be a Pirate, Toothless’s cowardice actually serves as a weird kind of compass. He’s the only one smart enough to be afraid when things get dangerous, which happens constantly once they reach the Isle of the Skullions.
Skullions are one of Cowell’s best inventions. They’re blind, deaf, and flightless dragons that hunt by smell. They are terrifying. They represent the first real "horror" element in the series, proving that these books aren't just for little kids. They’re about the brutality of nature.
Why This Book Changes the Berk Power Dynamics
In the first book, the focus was just on not getting eaten. By the time we get to How to Train Your Dragon Book 2, the stakes shift to the internal politics of the Hooligan tribe. Stoick the Vast, Hiccup’s father, is obsessed with the idea of "The Heir." He wants Hiccup to be a hero, but Hiccup’s heroism is intellectual.
There’s a specific moment in the book where they find the treasure, and it’s not just gold. It’s a riddle. Grimbeard the Ghastly left behind things that shouldn't be valuable—like a notebook—that turn out to be the most important items in the entire series.
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- The Second Best Sword: A weapon that Hiccup finds, which becomes his signature tool.
- The Mystery of the Dragon Tongue: Hiccup is one of the few humans who can speak Dragonese, a skill that is technically forbidden.
- The Rise of Alvin: This book establishes Alvin as a recurring nightmare, not just a villain of the week.
Cowell uses a very specific style of "found footage" storytelling. She writes as if she’s translating Hiccup’s actual memoirs found centuries later. This gives the narrative a layer of "truth" that most fantasy novels lack. You see his shaky drawings, his coffee stains, and his frantic notes in the margins. It makes the world feel lived-in. Berks isn't a shiny Viking utopia. It’s a cold, damp, smelly place where people have names like Dogsbreath the Dumb-Brain.
Breaking Down the "How to Be a Pirate" Training
The title of the book refers to a literal manual that the Vikings use. The "How to Be a Pirate" book within the story is actually just one page long. It basically says: "Get on a boat and yell at people."
This is Cowell’s way of satirizing the hyper-masculine, aggressive culture of the Vikings. Hiccup’s struggle is that he wants to read, he wants to think, and he wants to understand dragons instead of just shouting at them. This book introduces the idea that the "old way" of being a Viking is dying, or at least, it’s broken.
The climax takes place in a cavern filled with the aforementioned Skullions. It’s claustrophobic and genuinely tense. Unlike the movies, where the action is fast and aerial, the action in the books is often slow, tactical, and involves a lot of hiding in small spaces. Hiccup wins not because he’s the best fighter, but because he’s the only one who bothers to look at the map correctly.
The Real History Behind the Fiction
While the dragons are obviously fake, Cowell draws heavily from Norse mythology and the actual geography of the Inner Hebrides in Scotland. She grew up spending summers on an uninhabited island off the coast, and that isolation bleeds into the pages. When she describes the "Black Heart of the Ocean" or the jagged rocks of the Isle of the Skullions, she’s pulling from real-world maritime dangers.
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The series—and this book in particular—serves as a bridge for young readers moving from simple picture books to complex long-form storytelling. It deals with the concept of "The Thing," the Viking assembly where laws were made. It shows the messy reality of tribal leadership.
Actionable Takeaways for Readers and Parents
If you are coming to this book after watching the movies, you need to adjust your expectations. Don't look for a Night Fury. Look for a story about a boy who is tiny in a world of giants.
- Focus on the "Dragonese" Dictionary: Pay attention to the snippets of dragon language Cowell includes. It’s a fully realized, if silly, linguistic system.
- Track the Artifacts: The items Hiccup finds in the treasure chest in this book (the sword, the notebook) are not "Easter eggs." They are foundational plot points that don't pay off for another ten books.
- Appreciate the Illustrations: Don't skip the "bad" drawings. They are drawn by Cowell herself to look like a child's sketches, but they contain actual clues about dragon anatomy and weaknesses that Hiccup uses later.
- Compare the Villains: Compare Alvin the Treacherous here to his animated counterpart. The book version is much more of a "mirror" to Hiccup—he’s what happens when someone smart and small chooses malice instead of empathy.
The brilliance of How to Train Your Dragon Book 2 lies in its refusal to be a "standard" sequel. It doesn't just repeat the "boy meets dragon" beat. It expands the world into a pirate epic, introduces a truly terrifying villain, and deepens the mystery of Hiccup’s ancestry. It's a foundational text for the rest of the twelve-book series, setting up the eventual war between humans and dragons that the movies only hinted at in their final act.
If you’re starting the series now, take it slow. The humor is crass, the Vikings are rude, and the dragons are mostly pests. But by the end of this second volume, you’ll realize that Hiccup isn't just a Viking hero—he's the only person in his world who actually sees the big picture. That’s a much more powerful "superpower" than just having a fast dragon.
Next Steps for the Dragon Scholar
To get the most out of your reading experience, start a "Lost Things" list. As you progress through the series after Book 2, check off the items Hiccup recovered from Grimbeard's hoard. You'll find that Cowell is a master of the "long game" in plotting; nothing mentioned in the Isle of the Skullions is accidental. Also, try reading the footnotes aloud—they often contain the funniest world-building details that provide context for why the Hooligan tribe is so dysfunctional. This isn't just a kids' book; it's a masterclass in character-driven world-building.