Line a 5 x 9 inch (2L) loaf pan with overhanging plastic wrap. Gently crumble amaretti into large chunks (you should have about 1½ cups of coarsely crumbled cookies).
Whip cream using an electric mixer on high until it forms soft peaks. Pour in sweetened condensed milk and almond extract; whip on medium until well combined. Pour half of the mixture into prepared pan and smooth into an even layer, making sure that it fills the corners but not packing it in too tightly. Sprinkle crumbled amaretti in an even layer, right to the sides. Top with remaining cream mixture. Smooth into an even layer but do not pack down. Cover lightly with overhanging plastic wrap. Freeze for at least 6 hours and up to 2 weeks.
Place dried cherries in a small jar. Heat brandy and water in a small pot until very hot but not boiling. Pour over cherries. Cover and let stand at room temperature for at least 1 day; transfer to fridge for up to 2 weeks.
To serve, uncover semifreddo and flip onto a serving platter. Remove plastic wrap. Slice and top with cherries and brandy. Add more crumbled cookies and enjoy!
Nutrients per serving: 332 calories, 4 g protein, 14 g fat (7 g saturated fat), 48 g carbohydrates (1 g fibre), 41 mg cholesterol, 211 mg sodium
Best Health tip: Amaretti cookies are available in big supermarkets and Italian specialty shops.