Nutrition per serving may change if servings are adjusted.
2 cups golden raisins
1/4 cup Marsala, or dark rum
1 tablespoon butter
1/2 cup fat-free milk
2 tablespoons canola oil
1 tablespoon active dry yeast
1/2 cup lukewarm water
3 large eggs, divided
1/3 cup sugar
1 tablespoon freshly grated orange zest
1 tablespoon aniseed, crushed
1 tablespoon vanilla extract
1 teaspoon salt
3 cups all-purpose flour, approximately
2/3 cup confectioners’ sugar
1-1 1/2 tablespoons fat-free milk
2 tablespoons sliced almonds, lightly toasted
To make dough: Stir raisins and Marsala (or rum) in a medium saucepan over low heat until the fruit is heated through, about 3 minutes. Set aside to cool.
Melt butter in a small saucepan over medium heat. Swirl the pan until the butter turns a light brown, about 1 minute. Remove the pan from the heat and immediately add milk and oil. Cool to lukewarm and pour into the bowl of an electric mixer or a large mixing bowl.
Dissolve yeast in the water and add to the milk mixture. Lightly beat 2 of the eggs and add to the bowl along with sugar, orange zest, aniseed, vanilla and salt. Gradually stir in just enough of the flour to make a soft dough.
Knead the dough for about 6 minutes using a mixer fitted with a dough hook, or knead by hand for 10 to 12 minutes on a lightly floured surface. As you work, add just enough additional flour to make a smooth, elastic but still slightly sticky dough. (Do not add too much flour or the dough will not rise properly.) Drain the raisins and work in, a handful at a time, until well distributed in the dough.
Shape the dough into a ball and place in a large, oiled bowl; turn to coat with oil, and cover with plastic wrap. Let rise in a warm place until doubled in volume, 1 1/2 to 2 hours.
Lightly oil a baking sheet or coat it with nonstick cooking spray. Gently punch down the dough and transfer it to a lightly floured work surface. With a sharp knife, cut the dough into 3 equal pieces. Roll each piece into a 14-inch rope. Loosely braid the 3 ropes and firmly pinch the ends together. Transfer the braid to the prepared baking sheet. Loosely cover with plastic wrap and let rise in a warm place until doubled in volume, about 1 to 1 1/2 hours.
Preheat oven to 325°F. To glaze the braid, beat the remaining egg and brush 2 or 3 teaspoons of it over the dough; discard leftover glaze. Bake for 30 to 40 minutes, or until the bread is golden brown and sounds hollow when tapped on the bottom. Transfer to a wire rack to cool for 5 minutes.
To make icing: Whisk together confectioners' sugar and milk in a small bowl to make a thick but pourable icing. Drizzle over the warm bread and sprinkle immediately with almonds.