Cut a slit from top to bottom into the side of each jumbo olive. Ease the olive open slightly to insert about 1 teaspoon of cream cheese, forming a penguin belly.
Cut a small triangle-shaped notch out of 9 carrot rounds to form feet; press 1 triangular piece (trimming if necessary) into each small olive to create the beak.
Thread each jumbo olive onto a toothpick lengthwise through the existing holes. Anchor the toothpick onto a carrot slice (line belly up with feet); set a small olive on top (beak facing forward). Place penguins on a plate; refrigerate until assembly.
Combine shredded carrot, onion, pimento peppers, and celery in a bowl. Mix 2 tablespoons softened cream cheese, 1 teaspoon lemon juice, mayonnaise, and salt in a separate bowl; beat until fluffy. Fold carrot mixture into cream cheese; mix well. Refrigerate at least 1 hour before use.
Toss green apple slices, red apple slices, and 1 tablespoon lemon juice together in a bowl.
Cut carrot rounds into decorative shapes using vegetable cutters. Wrap in a wet paper towel and place in a plastic bag; refrigerate until assembly.
Pat cucumber slices dry. Place 1 half-slice tomato at the end of a cucumber slice; roll up together and secure with a toothpick.
Arrange 1/2 the carrot shapes in a bento box. Place 1/2 the sandwich spread in a small silicone baking cup; place 4 crackers in another cup. Arrange 1/2 the green apple slices, red apple slices, and grapes. Add 5 cream cheese penguins, 4 turkey slices, and 3 cucumber-tomato rolls. Use remaining ingredients to create a second bento box. Refrigerate until ready to eat.