1 pineapple - top trimmed
1 cup granulated sugar
1 vanilla bean, halved lengthwise
3 tbp packed dark-brown sugar
1 quart best-quality vanilla ice cream
1 liter club soda
Preheat oven to 425F.  Peel pineapple, reserving peels.  Cut flesh lengthwise into quarters.  Cut out and reserve core.  
Transfer peels and core pieces to large pot; reserve flesh.  Add 5 cups water, bring to boil.  Add granulated sugar and vanilla bean.  Cook, mashing peels occasionally with the back of a spoon to extract juice for about 30 min.
Cut pineapple into 1/2 inch cubes and transfer to rimmed baking sheet.  Sprinkle with brown sugar.  Cook until golden, about 20 min.  Transfer to bowl and let cool completely.  Cover and refrigerate up to 2 days.
Pour pineapple-peel mixture from pot through a sieve into a large bowl, discard solids.  Return liquid to pot and bring to boil.
Divide pineapple evenly among 8 serving glasses.  Top with 2 tsp syrup and 2 scoops ice cream.  Fill with club soda and drizzle with remaining syrup.
 
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