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Combine yeast and water in a small bowl. Let stand for at least 10 minutes until yeast turns foamy.
Place 2 cups flour on a working surface. Make a well in the middle of flour and add sugar, 1/3 cup butter, 2 eggs, vanilla extract and salt. Mix by hand, adding 2 cups flour ½ cup at a time until a smooth and lightly sticky dough is formed. Slowly add yeast mixture and milk, 1 tablespoon at a time to dough and knead for 5 to 7 minutes or until dough is completely smooth and elastic.
Shape the dough into a ball and transfer (crease side down) to a large oiled bowl. Brush a small amount of oil with hands over surface of dough. Cover with plastic wrap and place in a warm area for 2 hours or until dough doubles in size. Meanwhile, prepare chocolate paste.
Beat 1/2 cup butter with a hand mixer until smooth. Add remaining 1 cup flour and Abuelita chocolate and continue beating until completely mixed and a paste is formed. Divide chocolate paste into thirds.
Deflate dough by pressing with fingers. Divide dough in half.
Incorporate 2/3 chocolate paste in one half of the dough. Knead until dough changes color.
Line a large baking tray with parchment paper.
Roll 2 tablespoons dough in between palms of hand or on a surface making a 6 ½ to 7-inch-long strip. Repeat with chocolate dough. Twist both dough strips together, pinch ends together to form a circle or knot. Place on prepared baking sheet. Repeat until all dough is used, arranging the dough circles/knots in a larger circle (rosca shape). Dough twists make approximately 15-16 circles/knots. Optional: Wrap 3 small plastic baby figurines in the middle of a rolled out strip of dough. Make sure they are completely covered by dough.
Cover dough knots with plastic wrap and place in a warm area to rise for 30 minutes.
Preheat oven to 375° F.
Shape the remaining 1/3 chocolate paste into 3-inch strips between the palms of your hands. Arrange them around the formed rosca, over the dough knots. Arrange maraschino cherries around rosca in centers of knots.