1. Thread pineapple wedges lengthwise onto skewers. Set aside.
2. Place sugar and butter in small saucepan. Cook over medium heat, stirring occasionally, until sugar melts. Add rum and simmer 1 minute. Stir in whipping cream and vanilla, and simmer another 30 seconds. Turn off heat. Cover and keep warm.
3. On grill preheated to medium-high heat, grill pineapple skewers 2 to 3 minutes per side, until hot with light char marks. 
4. Transfer skewers to a plate and drizzle with rum caramel sauce, or serve sauce alongside for dipping.

Chef’s secret: If you don't have rum, replace it with brandy or bourbon. For added flavour, colour, and texture, sprinkle the grilled pineapple with chopped fresh mint and coarsely chopped pecans or roasted unsalted cashews. For added richness, dip grilled pineapple in melted chocolate.