Season pork tenderloins with salt and pepper. Place into a large bowl, cover, and refrigerate for 30 minutes.
In the meantime, place toothpicks in water to soak for 30 minutes so they don't burn on grill. You will need 8 wooden toothpicks.
Wrap 3 slices of bacon around each pork tenderloin and secure in place with toothpicks soaked in water. Place both tenderloins on grill over medium heat. Brush maple syrup onto each tenderloin and grill, brushing on maple syrup and turning often, until a meat thermometer placed in the center of the pork reaches 155 degrees F., about 20-25 minutes. (Internal temperature will reach 160 degrees F. upon standing).
Place tenderloins on a cutting board and let sit 5 minutes for easier slicing.