Roughly chop the cherries and combine them with the brandy in a microwave-safe bowl. Microwave 1 minute and then cool for 10 minutes. Drain the cherries and set aside. Chop chocolate into rough chunks, put into a bowl and set in the refrigerator to chill.
Combine the bread mix, yeast, milk, egg, butter and vanilla in the bread machine pan. Turn on the machine’s dough cycle and monitor how the dough is coming together for the first 3-5 minutes. If the dough looks sticky, add a tablespoon of flour at a time until it comes together nicely. Continue the dough cycle or turn off the machine once the dough has been through the cycle for about 15 minutes, has been kneaded well and the inside of the machine is warm. Allow the dough to rise until it has doubled – about an hour or until the cycle is complete.
OR to mix by hand or with a mixer and dough hook - combine ingredients in large bowl, then knead until soft, smooth, and elastic (turn out onto surface to knead, if necessary). Return to bowl, cover, and let rise in a warm place until doubled - about one hour.
Turn dough out onto a floured work surface and pat into an 8×10-inch rectangle. Pat the cherries dry with a paper towel and then sprinkle them on top of the dough. Take the chocolate chunks out of the refrigerator and scatter them on top of the dough. Roll up the dough to incorporate cherries and chocolate, and knead about 10 times or until evenly distributed.
Shape dough into a loaf, and place in a lightly greased bread pan. Cover with plastic wrap that has been sprayed with non-stick cooking spray and allow the dough to rise until it is just above the rim of the pan – about 30-45 minutes.
Bake in a preheated 350ºF oven for 30-35 minutes or until golden brown and sounds hollow when tapped. Let bread cool in pan for 5 minutes and then remove from pan and coo completely on a wire rack before slicing.
Bread will stay fresh for up to three days if kept in an air-tight container.