- 1 3 1/2- to 33/4-pound pineapple, peeled, cored, cut into 1-inch pieces
- 1/2 cup tawny Port (such as Quinta do Infantado)
- 1/4 cup maraschino liqueur (such as Luxardo)
- Large block of ice with orange slices and lime slices
- 2 cups chilled Prosecco or other sparkling wine
- 1 cup (or more) chilled sparkling water (optional)
Place pineapple pieces in large bowl. Pour brandy over; cover and let pineapple soak at room temperature at least 10 hours or overnight.
Place sugar in medium metal bowl. Using vegetable peeler, remove peel from oranges in strips (orange part only). Add orange peel to sugar and mash with muddler or handle of wooden spoon until sugar is soft and moist and turns light orange color, about 3 minutes. Add 1/2 cup boiling water and stir until sugar dissolves. Strain mixture, reserving orange syrup. Discard orange peel.
Strain pineapple mixture into large bowl, reserving brandy. Discard pineapple. Add 1/4 cup reserved orange syrup, lime juice, Port, and maraschino liqueur to brandy. Cover and chill at least 2 hours. DO AHEAD Can be made 1 day ahead. Keep chilled.
Just before serving, transfer punch mixture to punch bowl; add block of ice to bowl. Stir in Prosecco. Add 1 cup (or more) sparkling water, if desired, and serve.