Preheat oven to 350°F. Line a 9×5 loaf pan with parchment paper, leaving a slight overhang on two sides.
In a large bowl using a handheld electric mixer, beat the butter and sugar together until light and fluffy. Add in the eggs, half and half, pineapple juice, and vanilla. Beat in the flour, baking powder, and salt, until combined.
Pour half of the batter in the prepared pan, tapping it on the counter to evenly spread it out. Scatter half of the pineapple over the top.
Repeat with the remaining batter and pineapple.
Bake for 55 to 60 minutes, or until a toothpick inserted in the center comes out clean. Keep an eye on the bread toward the last 20 minutes of baking and loosely tent with foil if it seems to be over-browning.
Let cool in pan for at least one hour, then remove loaf from pan and transfer to a wire rack to cool completely.
Whisk together the powdered sugar, milk, and pineapple juice and pour over the cooled cake. Let set, slice, and serve!
Notes
Ensure to drain the crushed pineapple well to avoid a soggy bread.