Preheat oven to 350 degrees F (175 degrees C).

Line a rimmed baking sheet with parchment paper.

Arrange pineapple slices in an even layer on prepared baking sheet.

Roast pineapple in the preheated oven until tender, about 45 minutes.

Let cool until easily handled, about 20-30 minutes.

Transfer cooled pineapple to a container.

Pour rum over the roasted pineapple.

Split vanilla bean lengthwise and scrape the seeds.

Add vanilla seeds and scraped pods to the container.

Add raisins, cinnamon sticks, orange zest, vanilla extract, peppercorns, allspice berries, nutmeg, star anise, and cardamom.

Seal container and store in a cool, dark place.

Mix every day, removing any spice that becomes too dominant for your taste.

Continue until rum reaches desired flavor, 5 days to 2 weeks.

Strain through a fine-mesh sieve.

Strain again through a coffee filter.

Discard whole spices, reserving the strained fruit.