Wash all fruit (grapes, strawberries, blackberries) and gently pat dry to prevent sogginess in the cooler.
Lay out the tortillas and spread a thin layer of mustard on each.
Layer 2 ounces of deli beef and 1 cheese slice on each tortilla, then roll them up tightly.
Slice the rolled wraps into 1-inch thick pinwheels and thread them onto small wooden skewers for easy eating.
Pack the yogurt and creamy dip into small, leak-proof containers.
Assemble the fruit, cheddar cheese cubes, pickles, and beef skewers into a large bento-style lunchbox or individual containers.
Store the assembled boxes in a cooler with ice packs until ready to eat.