Stuffed Calamari in Tomato Sauce

I used to hate calamari when I was a kid. Really, it was just the tentacles that bothered me. Not gonna lie, I still don’t like them.

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It’s not a flavor thing, it’s really more the appearance. Too many legs. I have an issue with that. This is why I hate spiders. Too. Many. Legs. I even have a hard time taking apart crab legs because they look just like enormous spider legs. Squid tentacles don’t look like spider legs, but there’s still too many. But if you chop them up, you can pretend it’s something different. Hey, it works for me.

A while back I was gifted with a box of frozen squid. They were whole and therefore would need cleaning, a process I had never done before and had no idea how to do. I finally got that part figured out (process here!), and now it was time to deal with the tentacles. I chopped them up with glee, because I knew they were finally going to become part of this seriously delicious dish.

Unbeknownst to me, the tentacles were the least of my worries. As it turned out, the squid I had were a little small for how I wanted to prepare them. Usually, larger squid work great for stuffing because their size allows for you to get the filling into their body cavities easily. These were not so easy. At all. I think the Old Man finally forgave me for making him help me. Maybe. I mean, he loved the food and we’re still together, so I think that’s a good sign?

Some quick notes before you begin:

Get the right sized squid. If a size is not indicated on the package, look to see if they appear large enough for you to easily spoon in rice filling without having to repeatedly tell someone helping you that their thumbs are in the way.

Do not let your squid boil in the tomato sauce. You want to bring the heat up gently and allow it to simmer until the rice is done. Bringing up the heat too quickly can cause the squid to rupture and that kind of defeats the point of having stuffed calamari. The dish won’t be ruined, but still not what you’re aiming for here.

Don’t overstuff the body cavity. Keep in mind that the rice will expand. You want full, but not bursting. If it’s too hard to close the opening without a bunch of the filling squeezing out, you have too much.

When closing the opening with the toothpick, don’t worry about trying to keep it completely sealed. You need moisture from the sauce to be able to come in, you just want to keep the filling from spilling out.

If you realize too late that the squid you have is too small to stuff, consider cutting the body into rings and cooking those in the rice and sauce. It will still taste good!

If you have extra filling than what fits in your squid cavities, you have some options on how to use it. You can serve it as a side dish, just add more water as needed and cook until the rice is tender to your preference (add water 1/4 cup at a time to be sure it doesn’t get soupy). You could save it in the freezer to stuff other squid in the future, just keep in mind if you purchase more whole squid you’ll have more of those tentacles to deal with. Or you could stuff vegetables with the filling, just use the same process as this recipe here!

Stuffed Calamari in Tomato Sauce

  • Difficulty: the hardest part is getting the right size squid
  • Print

Ingredients

For the filling:

  • 1/4 cup olive oil, extra virgin preferred
  • 1/2 – 3/4 lbs yellow onion, sliced
  • 1/2 to 3/4 cup finely chopped parsley, packed
  • 1/2 cup finely chopped dill, packed
  • 1/4 cup raisins
  • 1 15-ounce can chopped tomatoes, pureed, divided into 1 cup and 3/4 cup portions
  • 1/2 cup white rice, any variety but not quick cooking
  • 1/4 cup white wine
  • 1/4 cup water
  • chopped tentacles from squid (roughly 1/2 pound)
  • salt and pepper to taste

For the sauce:

  • 1/4 cup olive oil, extra virgin preferred
  • 3/4 cup pureed diced tomatoes (from section above)
  • 1/2 water
  • 1/2 cup white wine
  • salt and pepper to taste

Directions

Prepare the filling. Put the olive oil and onions in a pan and sauté until the onions are lightly browned and translucent. Add all the remaining filling ingredients to the pan, using the 1 cup portion of the pureed tomatoes. Bring almost to a boil, stirring to prevent the ingredients from sticking, turn the heat down to a simmer and cover. Cook for 5 minutes.

Uncover the filling, stir, and cover again. Cook for another 5 minutes. Stir the rice, remove from the heat and allow to cool with the cover on. You do not need it to be cold, just cool enough to comfortable handle. The rice should be mostly cooked, but still a little firm.

Once the filling is cool enough, start filling the body cavities of the squid. This could be done in a variety of ways. You could spoon it in, or if you have a pastry bag with a wide enough opening you could squeeze the mixture in this way. If you don’t have a pastry bag, try putting the filling into a plastic storage bag then cut off one of the corners and squeeze the mixture into the bodies. Just a warning, things will get slippery so have patience (ha!).

Once each body has been filled, use a toothpick to hold the opening closed. See the pictures for how I did this. Be careful not to stab yourself! Put the olive oil for the sauce into a pan and smooth it around to coat the bottom. Put in the filled squid.

Put the remaining ingredients for the sauce in a mixing bowl (using the remaining 3/4 cup of pureed tomatoes) and combine. Pour the sauce mixture over the squid and cover. Turn the heat to medium and once the sauce begins to get hot drop the temperature down to maintain a gentle simmer. Cook until much of the sauce has been absorbed, the squid has puffed up, and the rice inside is tender. This should take about 30 minutes. If the sauce gets too dry, add water 1/4 cup at a time as needed to prevent scorching.

Once done, gently remove the squid from the pan. Any sauce can get spooned over the calamari. You will likely want a nice chunk of bread to help soak up any extra sauce because it will be way too good to let go to waste! Enjoy!

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