Nutrition per serving may change if servings are adjusted.
1 medium pineapple
4 large oranges, such as Valencia or blood oranges
2 tablespoons sugar
1/3 cup Port
2 tablespoons honey
1 teaspoon lime juice
1 cup seedless red grapes, halved lengthwise
8 large fresh mint leaves, slivered
Preheat broiler. Line a baking sheet with foil; set aside.
Peel pineapple, removing eyes. Cut into 1/2-inch-thick slices. Remove center core from slices with a 1-inch cookie cutter or paring knife.
Remove all peel and pith from 3 of the oranges with a paring knife. Cut crosswise into 1/2-inch-thick slices. Juice the remaining orange, discarding any seeds. Set aside.
Lay pineapple slices on one end of prepared baking sheet and arrange orange slices on the other end. Sprinkle with sugar. Broil, 4 to 6 inches from the heat, until the oranges are caramelized, about 5 minutes. (Watch carefully to prevent burning.) Removethe oranges with a spatula and set aside. Rotate the baking sheet and continue broiling until the pineapple is caramelized, 4 to 6 minutes more, removing any slices that are ready sooner.
Meanwhile, whisk Port, honey, lime juice and reserved orange juice in a small bowl.
To serve, place 2 pineapple slices in each of 4 shallow bowls. Arrange the orange slices over the pineapple. Top with grapes and pour honeyed Port over all. Sprinkle with mint. Serve immediately.