In a blender, puree the diced strawberries with 1 to 2 tablespoons water until thick and smooth. Using an electric mixer, whip the cream until soft peaks form, 3 to 5 minutes. Add the confectioners' sugar, vanilla and strawberry puree and continue whipping until slightly stiff peaks form, 1 to 2 minutes.
For each dessert, place a chocolate cookie on a plate. Dollop with 1 tablespoon of the strawberry whipped cream; gently press another cookie on top. Repeat, alternating cookies and whipped cream, to make a stack 6 cookies high, ending with a cookie. Wrap lightly in plastic wrap and refrigerate until the cookies soften slightly, 3 to 4 hours. Cover and refrigerate the remaining whipped cream.
Just before serving, use an offset spatula or butter knife to smooth the sides of the cakes. Top each cake with a few strawberry and banana slices and some of the remaining whipped cream. Drizzle with chocolate syrup. Sprinkle with peanuts and top with a maraschino cherry.