The Hopeful Puffin is almost completely round as "something kept on going wrong with the design". The mast is too long and leans to the left, causing the ship to go round in circles in a strong wind. It is stated in 'How to Speak Dragonese' that The Hopeful Puffin also has a leak, and that every half an hour Fishlegs or Hiccup had to "remember to bail out the seawater that had collected in the bottom of the boat"
The Hopeful Puffin is the ship that Hiccup and Fishlegs use in the Boarding-an-enemy-ship lesson at the beginning of the book. Hiccup states optimistically that "this boat can go a lot faster than you think. Looks aren't everything, you know...". The Hopeful Puffin seems to be able to keep up with the rest of the ships, however when she is rammed by Sparrowhawk, Snotlout and Dogsbreath the Duhbrain's ship, the Hopeful Puffin begins to spin around, causing Hiccup and Fishleg's to lose their way.
The Hopeful Puffin is also used later to escape from the Romans, however she starts spinning around in circles again and it takes around half an hour for the boys to be able to see where they are going. Fishlegs steers the boat back into the harbour because Hiccup is very depressed over the loss of his book 'How to speak Dragonese' and of Toothless.
It is mentioned as they draw nearer to Berk, that as the Hopeful Puffin has taken two big knocks (Firstly from Sparrowhawk and secondly from Hiccup jumping onto the deck from the Roman ship), she is taking on water "even faster than normal" and "despite Hiccup and Fishlegs bailing out the water as quickly as they could with their helmets", the Hopeful Puffin sinks when they are within 100m of the harbor.
At the end of the book Stoick tells Hiccup that "Gobber dived down into the Harbor and brought The Hopeful Puffin up for you" and that Gobber has mended some of the leaks in the boat. The Hopeful Puffin has been towed behind The Blue Whale, Stoick's warship. Camicazi, Fishlegs, Hiccup and Toothless sail the Hopeful Puffin back to Berk as the leaders of the triumphal procession.
When Hiccup and Camicazi go to Hysteria, to find 'The-Vegetable-That-No-One-Dares-Name', they drag The Hopeful Puffin behind their sleigh because, as Hiccup says, "It's getting so near to springtime, the ice may start cracking when we're out there. And if it does we're going to need some way of getting back across the Sullen Sea".
When escaping from Hysteria and the ice does crack, Hiccup, Norbert the Nutjob and Camicazi try to escape the Doomfang in The Hopeful Puffin, however this proves impossible and the Doomfang takes 'The-Vegetable-That-No-One-Dares-Name' and vanishes. Hiccup and Camicazi then return to Berk in The Hopeful Puffin.
- The Hopeful Puffin is one of four boats that belong to the Tribe Initiates that is actually named. The others are Snotlout's Sparrowhawk, Sharpknife and Tuffnut Junior's The Raven and Camicazi's The Stormy Petrel.
- The only time someone other than Hiccup steers The Hopeful Puffin while he is on board is when Hiccup is "depressed".
- Despite its suboptimal design, Hiccup had fond feelings about the boat, and named his sand yacht in How to Seize a Dragon's Jewel The Hopeful Puffin 2 after his old ship; this gave his identity away to Camicazi.
- Several times throughout the series, The Hopeful Puffin is used as an allegory.