Clean the squid thoroughly, removing the backbone and head. Separate the tentacles from the body. Leave the tentacles and the body, whole.
Brush the squid with the olive oil and season with salt and pepper. Place on a hot grill and mark on all sides. Grill until cooked through about 3 minutes.
In a bowl mix together the vinegar, lemon juice, extra-virgin olive oil, garlic, oregano, chile, salt, and pepper. Pull the squid from the grill and cut the body into inch-sized rings leaving the tentacles whole. Put the squid in the marinade hot. Mix well. Serve warm or chilled as a meze with a glass of ouzo.