Wash and prep the fruit and cut any large fruit into bite size pieces.
For the filling, place the cream cheese and sweetened condensed milk into a mixer bowl and whisk for a few minutes until the mixture is smooth and clump free.
Add the chilled heavy cream and whisk again, first on low speed, then on high speed for about 30 seconds until medium peaks form.
Add the strawberry extract (optional), strawberry preserves and a bit of food coloring, if desired. Whisk again for 10 to 15 seconds, just until combined. Do not over mix the filling - it will separate if overmixed!!
To assemble the fruit trifle: Pour the sangria into large bowl or shallow dish, for easier dipping. Soak a few ladyfinger cookies at a time briefly in the sangria, then arrange cookies in a single layer on the bottom of a large trifle bowl.
Top the cookies with a generous amount of creamy filling, then add a few handfuls of fruit on top. Repeat the process - layering the cookies, cream, and fruit - until the trifle bowl is full, finishing with a heap of fruit on top.
For best results, refrigerate the fruit trifle overnight. Keep refrigerated until ready to serve.