Place raisins, 1/2 cup amaretto and 1/2 teaspoon cinnamon in a small saucepan. Bring to a boil; reduce heat and simmer for 10 minutes or until excess liquid has evaporated. Let cool slightly, then puree in a food processor. Stir in remaining tablespoon of amaretto and let cool.
Puree in a blender or small food processor until smooth; set aside. Whisk together half-and-half, sugar, extracts and remaining 1/4 teaspoon of cinnamon in a large bowl.
Transfer to the container of an ice cream freezer and freeze according to manufacturer’s instructions. Remove paddle; cover and chill for 30 minutes until mixture is thick, but can still be stirred.
Drop spoonfuls of raisin mixture into ice cream; drag a rubber scraper through mixture to swirl.
Cover again and place in the freezer for several hours or until very firm. (May be made several days ahead.)