Frozen Pineapple Mojito
['1 fresh pineapple (about 4 pounds)', '1 cup white rum', '1/4 cup fresh lime juice', '1/3 cup mint leaves, plus more for garnish', '1 tablespoon (or more) sugar (optional)', 'Cocktail umbrellas', 'sliced fruit', 'flowers', 'maraschino cherries', 'and/or any other tiki drink decoration (optional)']
Trim top of pineapple to remove leaves, but leave top in tact. Cut pineapple in half crosswise. Run a knife in a circle around inside of halves 1/2" away from the skin. Cut across core of pineapple twice, creating 4 pieces and loosening the fruit. Using a big spoon or ice cream scoop, scoop out inside of each pineapple half. Place pineapple "cups" in freezer.
Discard core and finely chop pineapple (you should have about 4 cups). Place in a single layer on a parchment-lined sheet tray and freeze at least 1 hour.
Blend frozen pineapple, rum, lime juice, 1/3 cup mint, and 2 cups ice in a blender until smooth. Taste and add sugar, if needed.
Fill pineapple "cups" with mojito mixture, reserving extra for refills. Garnish with mint sprigs and tiki drink decoration, if using. Reserve remaining mojito mixture in freezer for second serving or serve in alternate glasses.
Pineapple "cups" can be hollowed out 3 days ahead; keep frozen. Pineapple chunks can be frozen up to 3 months ahead.
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