Preheat oven to 350°F (175°C). Grease a standard loaf pan.
In a large bowl, cream together the butter and sugar until light and fluffy.
Add eggs one at a time, mixing well after each addition.
Stir in the pineapple syrup.
In a separate bowl, whisk together flour, baking powder, and salt.
Gradually add the dry ingredients to the wet mixture, mixing just until combined.
Stir in the milk, then gently fold in the drained crushed pineapple.
Pour the batter into the prepared loaf pan and smooth the top.
Bake for 50 minutes, or until a toothpick inserted in the center comes out clean. If needed, bake an additional 5 minutes.
Let the bread cool in the pan for 10 minutes, then transfer to a wire rack to cool completely.
For the glaze, whisk together powdered sugar, pineapple syrup, and vanilla until smooth.
Pour the glaze over the cooled loaf. For a thicker glaze, let the bread cool completely before glazing. For a thinner glaze, drizzle while slightly warm.
Enjoy!