Caramelized pineapple is crispy on the outside, sweet, and fruity.
- Combine vanilla bean and liquid ingredients except rum and ¼ cup brown sugar.
- Heat over medium heat until sugar is dissolved and has thickened slightly, 15–30 minutes.
- Remove vanilla pod and let the sugar mixture sit at room temperature for 30 minutes.
- Dip pineapple into sugar mixture then dredge in remaining sugar, adding more as needed.
- Place pineapple on a greased baking sheet and place under broiler, shaking constantly until well browned.
- Remove pineapple; keep warm.
- Place baking sheet on two burners and heat over high heat. Add rum and ignite. Scrape browned bits off of pan and boil rum until reduced by half.
- Add rum to remaining sugar mixture and stir. Serve pineapple with remaining sugar mixture on the side.