in the bowl of an electric mixer, whisk together the cream, jam and sugar. beat on medium-high until soft peaks form, 2 to 3 minutes. beat in the amaretto and vanilla.
On a large plate, spread a thin layer of whipped cream in an 8-inch circle. arrange a quarter of the cookies on top, overlapping slightly, and spread 2 cups whipped cream on top. repeat with another layer of cookies and whipped cream. Sprinkle with half of the almonds and chocolate. layer again with cookies and whipped cream. top with remaining cookies; frost top and sides with remaining whipped cream. Sprinkle with remaining almonds and chocolate. refrigerate to soften, at least 8 hours or overnight.