I purchased whole squid and cleaned it myself so that we'd have plenty of tentacles as my daughter (she's four mind you) loves them. Half the tentacles went into the rice and the others cooked alongside the stuffed squid. I added some red wine to the rice mixture as it cooked and then poured some more over the stuffed squid just before baking it uncovered until tender, a mere 20 minutes or so ... and voila!
The only thing I regret is not asking for the squid's ink from my fish monger as I believe that with that ingredient the flavor of the dish would be taken to another level.
Makes 6 servings
2 to 2 1/2 pounds squid, cleaned well, tentacles removed and set aside
1/2 cup olive oil
1 large onion, finely chopped
3 cloves garlic, minced
1 1/2 cups rice
1 cup red wine
2 tomatoes, chopped
Small bunch parsley, chopped
Pinch of dried Greek oregano
2 1/2 cups water
2 tablespoons tomato paste, diluted in 1/3 cup water
Salt and freshly ground pepper, to taste
Chop half the tentacles, set aside and reserve the remaining tentacles intact with the whole squid pieces. Heat 1/4 cup of olive oil in a medium saucepan and cook onion until soft. Add the garlic, chopped tentacles and rice and cook one minute more. Add 1/2 cup red wine and boil for a minute or so. Stir in the tomatoes, parsley, oregano, salt, pepper and water and bring to a boil. Cover the saucepan; reduce the heat to low and cook about 15 minutes or so.
Remove the rice from the heat and allow to cool. Oil a baking dish and preheat the oven to 375 degrees. Begin stuffing the squid with the rice mixture, stacking each body in the baking dish as you go. Layer any remaining rice in the baking dish and nestle the squid amongst the rice. Add the remaining tentacles (which have been left intact) and pour the diluted tomato paste, 1/4 cup olive oil and 1/2 cup red wine over. Season well with salt and pepper and bake for 20 to 25 minutes until the squid is tender.