Preheat the oven to 350°F. Begin soaking raisins in Amaretto.
Using a stand mixer, whisk together yeast, 1 teaspoon sugar, and warm milk until well combined; allow to sit 5 minutes.
Add remaining 1/4 cup sugar, egg, 3 tablespoons agave, vanilla, salt, and butter, and mix using a dough hook for 1-2 minutes.
Add flour and mix on medium speed for 10 minutes or until dough is nice and elastic.
Remove dough from stand mixer and knead by hand for another 5 minutes. Place in a covered bowl and rise for 1 1/2 hours.
In a small bowl mix together the filling- brown sugar, cinnamon and drained raisins until combined.
Roll dough out into a rectangle, 1/4-inch thick. Brush remaining 2 tablespoons agave over dough. Sprinkle filling over dough.
Roll up and place in a greased loaf pan. Lightly cover and allow to rise in a warm area for 45 minutes.
Bake for 40-45 minutes or until deep golden brown and well risen. Cool for 30 minutes before removing to a wire rack to cool completely.