Preheat the oven to 350°F/180°C/Gas 4. Line cupcake pans with 14 cupcake liners and set them aside.
Using an electric standing or hand mixer, beat the cake mix, milk, eggs, oil, and chopped cherries until combined and smooth.
Use an ice cream scoop to divide the batter between the cupcake liners. Fill about ⅔ full.
Bake in the preheated oven for 20 minutes or until an inserted toothpick comes out clean.
Remove the cupcakes from the oven and let them cool in the pan for 5 minutes before transferring them to a wire rack to cool completely before decorating.
Pour the ½ cup of Captain Morgan Orange Vanilla Rum into a small bowl.
Carefully dip the top of each cooked and cooled cupcake into the vodka, shaking off any droplets. Set them aside.
To make the coconut frosting, use an electric stand or handheld mixer and beat the butter, powdered sugar, cream, and coconut rum together until creamy smooth, and stiff peaks form.
Using a medium ice cream scoop, scoop a mound of frosting on top of each cupcake. Use a small angled spatula to create a flat top.
Pour the sprinkles into a bowl and stir to combine.
Dip each frosted cupcake into the sprinkles to cover. Set them aside.
To make the pineapple-orange frosting, use an electric stand or handheld mixer, beat the butter, powdered sugar, and cream together until creamy smooth, and stiff peaks form.
Transfer half of the frosting to another bowl and set it aside.
Add the Malibu Pineapple Rum to the frosting in the mixing bowl, and whisk to combine.
Transfer it to another bowl and add a little yellow food coloring gel - remember you can always add more coloring but cannot take it away! Stir in the food coloring until well combined and you reach the desired shade.
Place the earlier reserved frosting into the mixing bowl, add the Orange Rum, and whisk to combine.
Add a little orange food coloring gel - remember you can always add more coloring but cannot take it away! Stir in the food coloring until well combined and you reach the desired shade.
Place a large star tip into a large piping bag. Add the yellow frosting down one side of the piping bag and the orange frosting down the other side. Gently squeeze to begin piping out the frosting so it mixes together.
Pipe a swirl of yellow-orange frosting on the top of each cupcake.
Top with a maraschino cherry and a little shredded coconut.
Fill 14 mini pipettes with spiced rum according to the package directions.
Insert each pipette into the cupcakes next to the cherry. Serve and enjoy!