Remove the tentacles and clean the calamari, leaving the bodies whole. Set the tentacles aside.
Place the calamari in an 8-quart pot and cover with water. Bring to a boil over high heat. Cook for 1 hour or until quite tender. Drain and cool.
Make the stuffing. Heat the olive oil in a 10-to 12-inch saute pan until smoking. Add the garlic and sun-dried tomatoes and cook until light golden brown, about 30 seconds.
Add the bread crumbs continue cooking until well mixed.
Allow to cool then stir in the basil, olives, fresh tomatoes and parsley.
Preheat the grill or broiler.
Stuff the cooled calamari with the bread crumb mixture and season with salt and pepper.
Brush the stuffed calamari and tentacles with 1 tablespoon of the oil and grill or broil until nicely charred, about 10 minutes, turning once.
While the calamari grills, place the tomatoes, remaining 3 tablespoons olive oil, and the chives in a small mixing bowl, and season with salt and pepper Arrange the calamari on a platter top with spoonfuls of the tomatoes, and serve.