In place of fresh pineapple, you can drain two 8-ounce cans crushed pineapple, roast it, and skip making the syrup.
Ingredients
Makes 81 pineapple (about 4 pounds), top trimmed
1 cup granulated sugar
1 vanilla bean, halved lengthwise
3 tablespoons packed dark-brown sugar
3 tablespoons dark rum
1 quart best-quality vanilla ice cream
1 liter club soda
Step 1
Preheat the oven to 425°F. Peel the pineapple using a sharp knife, reserving the peels as you work. Cut the flesh lengthwise into quarters; cut out and reserve the core. Transfer the peels and core pieces to a large pot; reserve the flesh.
Step 2
Add 5 cups water to the pot; bring to a boil. Add the granulated sugar and vanilla bean; cook about 30 minutes, mashing the peels occasionally with the back of a spoon to extract juice. Meanwhile, cut the pineapple into 1/2-inch cubes; transfer to a rimmed baking sheet. Sprinkle with the brown sugar and rum. Cook until just golden, about 20 minutes. Transfer to a bowl; let cool completely. Cover; refrigerate up to 2 days.
Step 3
Pour the pineapple peel mixture from the pot through a sieve into a large bowl; discard the solids. Return the liquid to the pot, and bring to a boil. Cook until reduced to 1/2 cup, about 4 minutes. Refrigerate the syrup, covered, until ready to serve, up to 2 days.
Step 4
Divide the pineapple evenly among 8 serving glasses. Top with 2 teaspoons syrup and 2 scoops ice cream. Fill with club soda. Drizzle with remaining syrup.Reprinted with permission from The Martha Stewart Living Cookbook: The New Classics by Martha Stewart Living Magazine, copyright © 2007. Published by Clarkson Potter, a division of The Crown Publishing Group.Buy the full book from Amazon.