Clean the squid: Pull out the head and tentacles and set aside. Using your index finger, remove and discard the clear cartilage from the inside of the squid. Remove and discard the viscera. If desired, using a small paring knife, remove and discard the squid’s purple membrane. Rinse the squid thoroughly. Take the head section aand cut away or squeeze out the mouth and eyes. Cut away any viscera that might still be connected. Rinse and drain.
Heat half the olive oil in a large skillet and saute the onions and garlic over medium heat until wilted. In the meantime, chop the tentacles. Add these to the onion mixture. Next, add the rice and saute. Add half the wine and simmer until absorbed. Season with salt and pepper.
Remove the rice mixture from the skillet and place in a mixing bowl. Add and mix in the pine nuts, raisins, and herbs. Adjust seasoning with salt and pepper.
Fill the squid about ? of the way with the rice mixture. Use a toothpick and secure close. Pour remaining olive oil into a large, wide pot. Place the stuffed squid in the pot snuggly. Pour in remaining wine and tomatoes and add enough water to come about ? of the way up the squid. Cover and simmer over low heat for about 40 minutes, or until the squid and rice are tender. Remove, cool slightly and serve.