In a large pitcher, add pineapple juice, cake-flavored vodka, and light brown sugar. Stir. Place in refrigerator to chill, stirring every so often to assure that brown sugar is dissolved. You can speed up the chilling process by putting the mixture in the freezer for about an hour.
To serve, swipe a slice of pineapple around the edge of a 9-ounce glass. (You can also just dip the rim in pineapple juice or water, but make sure to shake off the excess.) Dip the damp rim into a shallow plate of light brown sugar. Allow brown sugar to set-up for a minute or so. If you wish, add a pineapple slice and/or a maraschino cherry for a garnish.
Fill glass halfway with ice. Pour cocktail from pitcher overtop.
For a single mixed drink:
Swipe a slice of pineapple around the edge of a 9-ounce glass. (You can also just dip the rim in pineapple juice or water, but make sure to shake off the excess.) Dip the damp rim into a shallow plate of light brown sugar. Allow brown sugar to set-up for a minute or so. If you wish, add a pineapple slice and/or a maraschino cherry for a garnish. Fill glass halfway with ice.
In a cocktail shaker, add pineapple juice, cake-flavored vodka, and light brown sugar. Do not add ice to the shaker. The sugar dissolves more easily at room temperature. Shake for 10-15 seconds, or until sugar is dissolved. Pour over ice in prepared glass.
Notes
How long does this keep?Pineapple Upside-Down Cake Cocktails can be stored in the refrigerator for 3 days. The listed time difference of 1 hour to 5 hours is the time spent chilling in the freezer versus the refrigerator.Can I make this non-alcoholic?Yes! Simply omit the vodka and replace it with ginger ale and a teaspoon of caramel sauce for a refreshing mocktail drink that even the kids can enjoy.Can I make this with rum?You can make the drink with rum, but I would recommend against it unless you are looking for a very different flavor. Pineapple Upside Down Cake is traditionally made with vanilla or cake vodka and pineapple juice.