Calamari Stewed with Tomatoes

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 Tomatoes

Calamari Stewed with Tomatoes Recipe

  • Prep time: 15 minutes
  • Cook time: 1 hour, 20 minutes
  • Yield: Serves 4-6

You can buy frozen, cleaned squid in the freezer section of many grocery stores. Defrost by placing in refrigerator overnight, or in a bowl of ice water. This recipe does call for an anise-flavored liquor, which you can leave out if you want, but the dish will be better with it in.



  • 2 pounds cleaned calamari (squid), tubes sliced into rings and tentacles roughly chopped
  • 4 Tbsp olive oil
  • 1 sliced onion
  • 1 fennel bulb, chopped
  • 3 garlic cloves, chopped
  • 2 Tbsp 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


1 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.

2 Add the red wine, stir well, and increase the heat to high. Boil until the liquid is reduced by half.

3 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.

4 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.

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Showing 4 of 17 Comments

  • Katerina

    In culinary school they call it the 20/20 rule. Cook it for either 20 seconds or 20 minutes. Anything in between and it will be like rubber! I just love calamari.

  • Sara

    Can one do long-cooked calamari in a crock pot?

    I’ve never done it, but I am pretty sure it will work. I’ve stewed calamari like this in a low oven or on the stove for several hours and it was fine. Let us know how it works, OK? ~Hank

  • Nancy Singleton Hachisu

    Some people object to the texture of squid…personally I love it, especially not too cooked, or raw. But others find squid to have a fishy smell. The trick to getting rid of any lingering odors is to put the squid in a strainer and pour boiling water over it, then quickly plunge into ice water. This is a particularly good to try if one is thinking of eating the squid raw or perhaps just fried, with a squeeze of lemon and a pinch of salt. Lovely recipe and just in time for these cold winter days. I love the addition of Sambuca to pick up the fennel. Thanks, Hank.

  • J

    If you don’t drink, don’t add alcohol to anything. Is there a substitute or if one omits the alcohol and liquor altogether will this recipe still taste good? It sounds amazing. maybe I’ll just bite the bullet, omit and taste.

    The liqueur is important to get my flavors exactly, but a good substitute would be to grind 1 tablespoon of fennel seeds and add it when you would normally add the liqueur. ~Hank

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