Let the ingredients reach room temperature. Preheat the oven to 40 C for 10 minutes and close. In a large bowl, mix the warmed milk with 50gr of sugar and the yeast until dissolved. Add the flour and stir. Leave the yeast mixture in the oven for 40 minutes. In a small pot and over low heat, put the butter, the remaining sugar, the orange juice, the zest, the vanilla and the salt and stir until the butter melts. Remove the pot from the fire, add the liqueur, the wine and the slightly beaten eggs. Sift the flour and begin to gradually add the hot mixture alternating with the yeast. Knead the mixture until it reaches a soft doughy consistency. Set the dough aside and let sit in a warm spot for one hour, covered by a slightly-wet towel. Separate the dough into as many ‘tsourekia’ bread loaves as you desire, at least three or four. Place each loaf in a buttered round baking pan. Using a knife make a cross on the surface of the dough. Let sit for 40 minutes in a warm place so that the dough rises. In a small bowl, mix a little water with the egg yolk and lightly brush the surface of each loaf.