- 1 pound calamari, trimmed and cleaned (see Note)
- 2 1/2 tablespoons extra-virgin olive oil, divided
- Salt and coarsely ground pepper to taste
- 1 pound new potatoes, scrubbed, quartered if large
- 1 pound asparagus, ends trimmed
- 2 red bell peppers, seeded and sliced into thin strips
- 1 red onion, thinly sliced
- 1/3 cup black olives, pitted and coarsely chopped
- 1/3 cup small green olives, pitted and coarsely chopped
- 1/4 cup balsamic vinegar
- 1/4 cup coarsely chopped fresh basil, plus more to taste
- 2 cloves garlic, finely chopped
- 1 teaspoon crushed red pepper, or to taste
- Preheat grill.
- Lightly score one side of each calamari body in a crosshatch pattern with the tip of a sharp knife. Brush the calamari (bodies and tentacles) with 1 tablespoon oil and season with salt and pepper.
- Place the calamari on the grill over a medium-hot fire. Cover with a heavy object, such as a heavy skillet or a brick wrapped in foil. (Weighting the calamari ensures even cooking.) Grill for 2 minutes, flip and cook, weighted once again, until opaque, about 1 minute. Remove from the heat and set aside.
- Cook potatoes in boiling water just until tender when pierced with a fork, 8 to 10 minutes. Remove the potatoes from the water with a slotted spoon and set aside. Bring the water back to a boil and blanch asparagus just until tender, about 2 minutes. Drain and rinse well in cold water. Cut diagonally into pieces about 1 inch long, and set aside.
- Combine the reserved calamari, potatoes, asparagus and the remaining 1 1/2 tablespoons oil with bell peppers, onion, olives, vinegar, basil, garlic and crushed red pepper in a large bowl; toss well. Taste and adjust seasonings. Serve at room temperature.