Normally Hiccup would take more time to think. Not charge into town on Toothless’ back, speaking to no one as he snatched up a few supplies. As soon he stepped outside he was on the nightfury once more regardless of Astrid calling for him and they were rocking skyward, leaving the girl standing dumb in their stead. By the time she would mount her dragon the two of them would already be gone. 

Hiccup peered through his spyglass as they lifted over the trees and urged Toothless forward towards the distant shore. There was a small speck in the distance that gradually shaped into a boat the closer they flew, the wind carried them higher over the quiet sea and he peered down at the enemy Vikings upon the ship. Only drawn from the sight when Toothless snarled at three dragons that were about to confront them. They seemed to hesitate though and Hiccup was about to discarded them as a threat when suddenly they rushed forward.

He lead them upward, Toothless by far superior in speed. 

Then circled around- blasting the dragons with a plasma bolt that knocked their formation apart. With narrow pupils Toothless continued his dive through the scattered group and swooped low over the deck, grabbing one of the Vikings and flinging the man into the sea before rising high again. Hiccup patted Toothless as they burst through the cloud cover disappearing from sight of the ship. “If we deal with the Vikings we should be able to bring those dragons around…”

Toothless didn’t entirely agree with that but disliked the Vikings below for their enslavement of his kind- how could he not? So attacking he had no problem with.