First, pour 1/2 cup of chia seeds, 2 cups of coconut milk, 1/2 teaspoon of vanilla extract, and 4 tablespoons (1/4 cup) of maple syrup in a large mixing bowl and stir until ingredients are well combined. Pour combined ingredients into a container with an air tight seal and put in the fridge overnight (minimum 2 hours).
Next, get your chia pudding out of the fridge and scoop it into the blender and blend on medium speed for 30 seconds or until all of the chia seeds are finely chopped. To make to pudding light and fluffy: pulse the blender on and off while blending, not letting the blender stay on for more than a few seconds at a time.
Then, pour the pudding from the blender into a mixing bowl and add 1/2 cup of shredded coconut and stir until well combined. Place back into the fridge, covered, for 1 hour.
Next, finely chop 1 1/2 cups of pineapple and toss into a mixing bowl. Add 1 tablespoon of maple syrup and 1 tablespoon of shredded coconut and stir until well combined. Pour pineapple mixture into the bottom of a serving bowl, making sure to distribute the pineapple evenly across the bottom. Cover and place in the fridge for 1 hour.
Finally, get your pineapple and pudding mixtures out of the fridge. Uncover them and pour your blended coconut chia pudding over the top of the pineapple mixture in your serving bowl. Sprinkle 1 tablespoon of shredded coconut across the top of the pudding. Serve immediately or place in the fridge, covered, until ready to serve.