I do not own HTTYD
Hiccup taught Toothless to fly after only one week being down.
He and Toothless went exploring and found the dragon island. There were several children camping there who called themselves misfits.
After visiting most afternoons and having killed the 'queen' they were visited by a priestess who said that she had blessed the island and that if there was a settlement here it would house all the misfits of other villages.
There would be two levels of living in the place. The lower level would be the Jacks they would be trained in every art known to the village for two years, until they were granted a great gift or talent by the priestess, signified by the apparition of a symbol of their talent over their head and the changing of one eye's color. Hiccup had already been training in several arts at Burk and was graced almost immediately with Forge, and transformation. He could turn into a dragon.
Hiccup was soon made village leader and married Toothless who, it turns out, was a girl. Hiccup had a daughter a year after he had disappeared from Burk. He named her Asia.