In a blender, combine fresh strawberries and ¼ cup of pineapple juice. Blend until smooth, about 30 seconds.

Pour the strawberry mixture into a jug and set aside.

Rinse blender, then add fresh pineapple, ice cubes, the remaining pineapple juice, and coconut milk. Blend until creamy, about 30-45 seconds.

In a tall glass, start by adding the strawberry base to about 25% full.

Gently pour the coconut-pineapple mixture over the back of a spoon into the glass to maintain separation.

Use a straw or skewer to lightly swirl the layers, garnishing with a pineapple wedge and a fresh strawberry.