Prepare cake layers: Preheat oven to 350°F. Grease pans, line with parchment, and sift flour, baking powder, and salt. Whisk egg whites and milk in a separate bowl.
Cream butter with paddle attachment, gradually add sugar until light and fluffy. Mix in cream of coconut and coconut extract. Scrape the bowl as needed.
Alternate adding flour mixture and egg white/milk mixture, starting and ending with flour. Beat until smooth on medium-low speed after each addition.
Divide batter between pans. Bake 6-inch cakes for 30 mins or 8-inch cakes for 35-40 mins until a toothpick comes out clean. While hot, press a lint-free towel on top to level. Be cautious due to steam. Let cool, then cut in half.
Create buttercream: In an electric mixer, combine butter and confectioners’ sugar on low. Gradually add heavy cream until spreading consistency. Add rum extract and whip until fluffy. Transfer half to a piping bag.
Assemble: Crush and pat dry pineapple chunks. Pipe a line of frosting on a cake layer, add rum frosting, and pineapple. Repeat for layers 2 and 3. Top with another layer, frost but skip pineapple. Layers 4, 5, and 6: buttercream and pineapple, then top with buttercream.
Apply a thin crumb coat and chill.
Make blue curacao frosting.
Add blue curacao, orange extract, and blue food color to the remaining frosting. Whip and adjust sugar as needed. Transfer to a piping bag.
Pipe blue frosting on the bottom 2/3 of the cake and white rum frosting on top. Smooth with a spatula.
Pipe swirls of leftover rum buttercream on the cake's top edge.
Garnish with cherries and pineapple slices. Store in the refrigerator. Serve at room temperature.
Apply a thin layer of frosting on the entire cake (crumb coat) and chill.
Save leftover rum buttercream.
Make blue curacao frosting.
Add blue curacao, orange extract, and blue food color to the remaining frosting. Whip until well incorporated. Add more confectioners' sugar if needed. Transfer to a piping bag.
Pipe blue frosting around the cake's outside, then finish with white rum frosting. Smooth with a spatula. Use a bench scraper to even the sides.
Chill the cake until firm, about 30 mins to 1 hour. Smooth the frosting with a warmed spatula.
Pipe swirls of leftover rum buttercream on the top edge of the cake.
Garnish with maraschino cherries and fresh pineapple slices. Store in the refrigerator, bring to room temperature before serving.