Using a sharp knife, cut around the perimeter inside each pineapple about 1/2 inch from the skin, leaving a sturdy shell (do not cut through the exterior).

Scoop out the pineapple flesh with a spoon or melon baller into a bowl. Reserve about 3/4 cup of the chunks per pineapple for garnish and the rest can be used in the blended base.

Trim any excess interior so the shell sits flat. Pat the inside of the shells dry with paper towels and place them in the freezer upright for 10–15 minutes while you make the piña colada. Chilling prevents melting quickly when you pour the frozen mixture in.

Make Frozen Piña Colada

If your pineapple chunks are not frozen, spread the fresh chunks on a tray and freeze 30–60 minutes so they are very cold; this improves texture. Alternatively use frozen pineapple.

In a high-speed blender, add 2 cups frozen pineapple chunks, 1 cup pineapple juice, 1 cup cream of coconut, 4 tbs white rum, 1/2 cup vanilla or coconut yogurt (if using), and 2 cups ice cubes.

Blend on high until completely smooth and thick. Stop and scrape down the sides as needed. The mixture should be scoopable but still pourable—similar to soft-serve. If too thin, add a handful of ice or frozen pineapple. If too thick, add 1–2 tbs pineapple juice or 1 tbs simple syrup to loosen.

Taste and adjust sweetness with simple syrup (up to 1 tbs) and brightness with a squeeze of lime if desired. If serving alcohol-free, omit the rum and add 2–3 tbs extra pineapple juice or coconut water.

Assemble & Garnish

Remove pineapple shells from freezer. Using a large spoon, fill each chilled pineapple shell with the frozen piña colada mixture, packing gently to eliminate large air pockets, and mounding slightly above the rim.

Top each filled pineapple with about 3/8 cup (roughly half of the reserved fresh pineapple chunks per shell) of fresh pineapple pieces so there is a fresh fruit contrast.

Sprinkle 1.5 tbs toasted coconut flakes and 1 tbs shredded unsweetened coconut over each serving for texture and visual appeal.

Garnish with a mint sprig, a maraschino or fresh cherry on top, and a pineapple lid tilted on the side or placed as a hat. Serve immediately with a straw and a long spoon.

If preparing slightly ahead, keep filled pineapples in the freezer no longer than 20–30 minutes to avoid cracking the shells from expansion; otherwise store the blended base in the freezer in an airtight container and re-stir before serving.