Preheat oven to 350°F. Line a 9×5-inch loaf pan with parchment paper, leaving some overhang for easy removal.
In a large bowl, cream together softened butter and sugar until light and fluffy using a handheld mixer.
Beat in eggs, half-n-half, pineapple juice, and vanilla until combined.
Add flour, baking powder, and salt, mixing until the batter is smooth.
Pour half of the batter into the prepared loaf pan and tap gently to level.
Scatter half of the crushed pineapple over the batter, then repeat with remaining batter and pineapple.
Bake for 55–60 minutes or until a toothpick inserted into the center comes out clean. Tent with foil during the last 20 minutes if browning too quickly.
Cool in the pan for 1 hour, then transfer to a wire rack to cool completely.
In a small bowl, whisk together powdered sugar, milk, and pineapple juice until smooth.
Drizzle glaze over the cooled bread. Let set, slice, and serve.