After Hiccup and Toothless left Berk in search of new islands, they had soared in the sky seemingly getting nowhere but the endless blue sea.

It had seemed their search was finally over when they landed on an island that wasn't marked on the map. Though, they had been knocked unconscious.

When the brunette haired boy awoke, he found himself and his nightfury in a cell. Toothless was held down by various chains on his wings, snout and limbs. Hiccup was chained by his arm and leg. The cell around him was a bit small, the walls were a dark limestone with moss on certain bricks. The cell door was made up of pure obsidian. His friends had no idea he and Toothless were missing.