Squid can be cooked one of two ways: For the blink of an eye, or for a long, long time. Anything in between and it is rubbery.
This dish, which is our version of a Southern Italian classic called calamari in umido, takes the long view of calamari cooking.
Think of this dish as something between a stew and a pasta sauce. It’s every bit as good as-is—with crusty bread, of course—as it is accompanying pasta (go with a short pasta like penne, bowties or fusilli) or, even better, a creamy polenta.
You can even add a little cheese to the polenta, if no one’s looking. Italians rarely mix seafood and cheese.
Calamari Stewed with Tomatoes
- 2 pounds cleaned calamari (squid), tubes sliced into rings and tentacles roughly chopped
- 4 tablespoons extra virgin olive oil
- 1 sliced onion
- 1 fennel bulb, chopped
- 3 garlic cloves, chopped
- 2 tablespoons tomato paste
- 1/4 cup Sambuca or other anise-flavored liquor
- 1 cup red wine
- 1 28-ounce can of crushed tomatoes
- Salt and pepper
- 1/2 cup parsley, chopped
- 1/4 cup fennel fronds, chopped
Sauté onions, fennel, garlic:
Heat the olive oil in a large pot over medium-high heat. When the oil is hot, add the onions and fennel. Stir to coat with oil and sauté, stirring occasionally, until it begins to color, about 5-6 minutes. Sprinkle some salt over it.
Add the garlic cloves and tomato paste and stir well to combine. Cook this for another 2-3 minutes, stirring once or twice.
Add the red wine:
stir well, and increase the heat to high. Boil until the liquid is reduced by half.
Add the Sambuca or other anise-flavored liquor, and the crushed tomatoes.
Stir in the calamari and bring the pot to a gentle simmer:
Simmer for at least 1 hour. After an hour, taste a piece of calamari; It should be tender. If it’s not, keep simmering. Check for tenderness every 15 minutes afterward.
Season to taste with salt and pepper:
Once the calamari is tender, taste the stew for salt and pepper, adding if needed. Add the chopped parsley and fennel fronds. Stir well to combine and serve.