Combine milk, cream, cookies, 8 tablespoons sugar, and vanilla bean in a medium saucepan and bring to a simmer. Turn off heat and let rest for 5 minutes. Bloom gelatin in a bowl of cold water. Puree the amaretto cookie mixture. Remove gelatin, combine with all other ingredients. Pass through a chinois. Cool and pour into 4 individual ramekins. Refrigerate until set, about 1 1/2 hours. Combine cherries, Vin Santo, and 1/4 cup sugar in pot. Simmer for 5 minutes. Remove from heat and let cool.
To serve, turn each ramekin upside-down over a dessert plate to release panna cotta. Top with a spoonful of marmallata.
This recipe was provided by professional chefs and has been scaled down from a bulk recipe provided by a restaurant. The Food Network Kitchens chefs have not tested this recipe, in the proportions indicated, and therefore, we cannot make any representation as to the results.