- 2 tablespoons olive oil, divided, or as needed
- 1/2 cup diced onion
- 1/2 cup diced red bell pepper
- salt and ground black pepper to taste
- 6 ounces spicy Italian sausage, removed from casings and crumbled
- 4 ounces calamari tentacles, minced
- 1/4 cup chopped fresh flat-leaf parsley
- 1 large egg
- 1/8 teaspoon smoked paprika
- 1 1/2 pounds cleaned calamari tubes
- 18 toothpicks, or as needed
- Heat 1 tablespoon olive oil in a skillet over medium heat. Cook and stir onion and red pepper with a pinch of salt in hot oil until onion is soft and translucent, 5 to 7 minutes. Remove from heat and cool to room temperature.
- Stir sausage, minced tentacles, onion mixture, parsley, egg, smoked paprika, salt, and pepper together in a bowl until evenly combined. Transfer mixture to a piping bag.
- Pipe sausage mixture into tubes, filling about each tube about 2/3 full. Thread a toothpick through the top of each tube to fasten the opening together. Place stuffed tubes on a plate, cover the plate with plastic wrap, and refrigerate until completely chilled, about 1 hour.
- Preheat an outdoor grill for medium-high heat and lightly oil the grate.
- Brush tubes with remaining olive oil to coat on all sides and season with salt.
- Cook stuffed calamari on the preheated grill, turning occasionally, until stuffing is cooked through, 10 to 12 minutes. An instant-read thermometer inserted into the center should read at least 155 degrees F (68 degrees C).