Combine sugar, yeast and milk and allow mixture to sit for 4 to 6 minutes or until mixture is bubbling and foamy.
Combine flour and salt in a stand mixer bowl and whisk together. Create a well in the center of flour mixture and add yeast mixture.
Mix together with paddle attachment until a ‘shaggy’ dough forms.
With the mixer on medium speed, add eggs, one at a time, followed by vanilla.
Add butter, in a slow and steady stream, until fully combined and a sticky, wet dough has formed.
Cover and store in a in a warm area to rise until doubled in size, about 1 hour 30 minutes.
Uncover, fold in pearl sugar, re-cover, and allow dough to rise again for about 30 minutes.
Heat waffle iron and scoop 1/3 cup batter into each well and press until each waffle has nicely browned and caramelized.
Carefully remove from waffle iron and transfer to a cooling rack.
Repeat steps 8 and 9 until all batter has been used.
Allow waffles to cool completely and melt chocolate over a double boiler.
Dip top of each waffle with melted chocolate, shaking off any excess.
Place dipped waffles, bare side down back onto the cool rack and sprinkle with sea salt flakes.
Allow chocolate to cool and harden. Serve.