In a large bowl, combine the instant vanilla pudding mix, Cool Whip, whipped cream cheese, and the crushed pineapple (with its juice). Stir everything together until it’s beautifully light, fluffy, and completely combined.

Chill the bowl into the fridge until you're ready to serve.

Prep for Assembly: About 30 minutes before your guests arrive, line up your plastic wine glasses and gather your garnishes (toasted coconut, cherries, pineapple wedges, wafers, and umbrellas).

Build the Cakes: Press one round sponge cake dessert shell into the bottom of each plastic wine glass.

Top the cake with two large scoops of the pina colada dip. Sprinkle a generous pinch of toasted coconut over the top. Garnish with a maraschino cherry, a fresh pineapple wedge, and a vanilla wafer cookie.

Pop a mini cocktail umbrella into each glass, arrange them on a fun serving platter with spoons nearby, and get ready for the compliments!