In the bowl of your stand mixer, dissolve the yeast in warm milk and let it sit for about 5 minutes until frothy.
Add sugar and salt. With your dough hook attachment, at low speed, mix to combine.
Melt the butter and cool until room temperature, or cool to the touch. Add to the yeast mixture.
Add the eggs, one at a time, with the mixer at low speed, to the yeast mixture. Slowly add the flour one cup at a time until a soft dough forms and pulls away from the side of the bowl.
Knead the dough on a lightly floured surface until smooth and elastic. Place it in a greased bowl, cover with a cloth, and let rise in a warm place for 1–2 hours or until doubled in size.
In a small bowl, mix together the sugar, brown sugar and cinnamon. Punch down the risen dough and roll it out on a floured surface into a 16x20 inch rectangle. Spread the softened butter over the dough and sprinkle the cinnamon-sugar mixture evenly. If adding nuts or dried fruits, sprinkle on top of the cinnamon-sugar mixture.
Roll the dough tightly from the long side, forming a log. Place the rolled dough, seam side down, on a parchment-lined baking sheet and shape it into a circle, connecting the ends to form a ring. With clean scissors, make cuts two-thirds through the ring at 1-inch intervals. Gently turn each section on its side. Let rise while the oven preheats.
Preheat your oven to 350°F. Bake the tea ring for 25–30 minutes or until golden brown.
Allow Tea Ring to cool on the baking sheet for 10 minutes before transferring to a wire rack to cool completely.
In a small bowl, whisk together the powdered sugar, milk, almond extract (optional) and vanilla extract until smooth. Drizzle over the tea ring. Cut the red candy cherries in half and place at intervals on the top of the ring. Cut the green candied cherries in quaters and place around the red cherry to create a Holly decoration.