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Running away from everything you've ever known, for most people, would probably incite a greater internal conflict than what Hiccup's dealing with, but—well. Hiccup’s never been accused of being most.
It's not like it doesn't hurt. There's a wound somewhere, raw and tender, the culmination of every soft, complicated thing that kept him tied to Berk for so long, but—
It feels like the kind of wound that he knows will heal the moment it opens, one reminiscent of all the scraped knees and scratches he ever got running through the woods searching for trolls or a new type of plant. A kind of wound that bleeds in colours of moving on and the bigger, wider world and the feeling that a million things have made you who you are, and more than some of them hurt, but you'll someday be bigger than each one.
That is to say, Hiccup looks back at Berk as he flies further and further away, with all of its torch lights like upside-down stars and its hills and the paths he knows better than he knows the lines of his palms, and he doesn't feel as sad as he should.
He'll miss Gobber terribly, he knows—already does, really—and the cove where he and Toothless made a little home for themselves. The forge and the ocean views from sky-high cliffs where you can't help but wonder what there is in all that blue that you're not seeing.
Hiccup will miss his father. He will. Stoick hurt him a lot, more than he's still willing to admit in words, but Stoick also loved him.
Hiccup thinks so, at least, in his own, convoluted way.
It just can't make up for the pain he caused. That Berk caused. It's weird that Hiccup never really noticed before, how much it all truly piled up inside him, but it's impossible to ignore now, and—
It's so much wasted space. Hiccup won't kid himself that he's got any self-esteem, but if nothing else he knows he's got ideas and he knows he's stubborn enough to make them work. They just need the room to grow, and he can't do that when he's being torn down for every small mistake.
There's so much out there. There's got to be things for Hiccup to find. Things to do.
Hiccup will miss his father, sometimes, he's sure—but there's something telling him that he'll be gladder to have gotten away. Hiccup thinks he came from beasts. It's time to find them again.
So there's a dull ache that he could press if he wanted to, and he probably will sometime in the not-so far-off future, but the feeling of undefined, unrestrained freedom wins out. Toothless' wings beat on either side of him, strong and sure, and he feels his foot settled in the strap for the tailfin and the sky is everywhere. Each breath seems to fill his lungs to the brim. He could go so, so far and there's no one here to stop him.
He's never going back to Berk ever again. He's free.