Build the sandwiches: Lay out 8 slices of white bread. Top 4 of the slices each with 1 lettuce leaf, 2 oz of deli roast beef, 1 slice of cheddar cheese, and 2 slices of tomato. Place the remaining bread slices on top and cut in half.
Prepare the fruit: Wash and thoroughly dry the 1 cup of green grapes and 1 cup of red grapes. Pack them into a crush-proof container.
Mix the trail snacks: In a small bowl, combine the 1/4 cup dried cranberries, 1/4 cup dried cherries, 1/2 cup roasted peanuts, and 1/2 cup granola. Transfer the mixture to a sealed bag or container.
Pack the cooler: Place the 4 chocolate chip cookies in a rigid container. Load the sandwiches, prepared fruit, snack mix, cookies, 2 cans of sparkling water, 2 canned sodas, and 2 fruit puree pouches into a cooler or insulated basket alongside cold ice packs.