Rinse the strawberries, remove the stems, and cut into small pieces.
Cut the pineapple into small pieces. Puree the pineapple with the strawberries, vanilla, and buttermilk in the blender.
Pour the drink into 4 glasses, or you can serve the shake in a hollowed pineapple halve. Serve garnished with skewers of fresh fruit (such as cocktail cherries, pineapple balls, etc.).