It was bound to happen.
Lesson learned: Don't try a new trick over the ocean…ever.
"Alright Bud, let's go." Hiccup whispered in the ear of his rare, powerful, Night Fury, named Toothless. Being the most intelligent type of dragon known to Vikings, he understood what he meant. Arching back a bit, to gain some speed in the flight, he leaped up in a vertical takeoff. Having the picture of the trick in his mind, Hiccup tugged on his saddle, turning his dragon far right. As he tugged, he also pushed downward with one hand, and pulled up with the other, making him spin.
Twirling around and around and around in the air, over the ocean. Over Berk. Down below, the folk could make out a black shape in the sky, doing a trick of spinning that might have looked like the spinning of a spear thrown sideways. It awed the Vikings below, and the noise of them lured the chief, and the rest of the teens on Berk, to come out and investigate. "What in Thor's name is he doin' ?" shouted the Chief, Stoick the Vast, who just happened to be Hiccup's father.
Fishlegs gasped in surprise "He doing the Half Turn Pike, a tricky yet not impossible, trick. You see, you have to-" he started, only to be interrupted by Snotlout. "Yeah yeah yeah, no one cares about that." He said, watching the dragon and rider with a stern face, probably made of jealousy. Astrid laughed. Of course, out of all times, Snotlout had to be jealous, after winning the Tawfest games not just a few days ago. The twins, Ruffnut and Tuffnut, just watched with anxious faces, as if hoping he would make toothless shoot fire at one of the many houses, setting it ablaze. Knowing Hiccup, Astrid knew he wouldn't dare try something like that. After a few more minutes of tricks and turns, the towns people were starting to get tired of standing in the same place, and started to go about their day. The rest of the teens were starting to get bored as well. The twins (seeing that they weren't going to wreck anything soon) had left, most likely to their Hideous Zippleback, Barf and Belch. Snotlout and Fishlegs returned to the Academy, Fishlegs still going on how to do the 'difficult, yet not impossible' trick. Astrid shook her head at all of them. Stoick took one last look at the riding pair, and then went off to do Chief stuff. Only Astrid stayed. She wanted to see how he had done the trick, eager to best him in any upcoming trick competition…he won every time.
She raced into her house, grabbing a bear skin coat, for it had gotten chilly outside, then ran out to the docks. She climbed up to the top of the catapult that was located there, hoping to get a better view. As the wind rushed past her, blowing the strands of hair that went tucked in a braid or in her head band away from her eyes, she noticed something. Toothless had stopped spinning (most likely from dizziness). He spread out his wings, hoping to gain balance, only to have to wind push them off coarse. Astrid knew what was going to happen before it did. She opened her mouth to say something, just as the wind knock Hiccup and Toothless into a rock (many high ones were located just off shore; boats were ordered not to try and sail there obviously) The two rings that connected to Hiccup's saddle, keeping him on, unlatched. He fell into the water, Toothless following. Having none to guide his tail, he fell with panic, spinning around, until they both crashed into the waves.