Preheat an outdoor grill for medium heat and lightly oil grate.
Cut the peaches in half, removing the pit. Keeping the skin on the pear, cut straight down one side, then the opposite, leaving the core. Cut the two remaining sides off of the core (the pieces will not be even).
Brush a small amount of oil on the pineapple, peaches, and pear to prevent them from sticking to the grill. Sprinkle all sides of the fruit with pepper. Place the fruit flesh side down on the grill and cook for 10 minutes, turning as needed, until soft and caramelized.
When the fruit is cooked, remove from the grill and place on a serving platter. Sprinkle with crumbled cheese and top with chopped basil, parsley and arugula. Drizzle with olive oil if desired. Serve hot.
