Wash, peel, and slice the cucumbers into ½-inch thick rounds. Discard the ends.
Using a small measuring spoon or melon baller, carefully scoop out a small portion from the center of each cucumber slice, creating a shallow well.
In a medium bowl, combine the softened cream cheese, mayonnaise, ranch dressing, Italian seasoning, and garlic salt. Mix until smooth and creamy.
Stir in the chopped fresh dill until evenly distributed.
Transfer the filling to a piping bag fitted with a star tip.
Pipe approximately one tablespoon of filling onto each cucumber slice.
Slice each cherry tomato in half and place one half on top of each filled cucumber.
Sprinkle with freshly ground black pepper.
Serve immediately or chill until ready to serve. These cream cheese cucumber bites taste even better when slightly chilled.