Preheat the oven to 350°F (175°C). Grease a 9x5-inch loaf pan and line it with parchment paper for easy removal.
In a medium bowl, whisk together the flour, sugar, baking soda, salt, and cinnamon.
In a large bowl, mix the mashed bananas, crushed pineapple, oil, eggs, and vanilla until well combined.
Add the dry ingredients to the wet mixture and stir just until combined. Fold in the chopped pecans gently.
Pour the batter into the prepared loaf pan. Bake for 55–60 minutes, or until a toothpick inserted into the center comes out clean. Let it cool in the pan for 10 minutes, then transfer to a wire rack to cool completely.
In a mixing bowl, beat the cream cheese and butter until smooth. Add the powdered sugar and vanilla extract, then mix until creamy. Add milk, 1 tablespoon at a time, to reach your desired consistency.
Once the bread has cooled, spread the cream cheese frosting evenly on top. Sprinkle with extra chopped pecans if desired.