Apparently it's a Southern Italy tradition to eat seafood on Christmas Eve as part of the Feast of the Seven Fishes. However, I only realized this after I had already decided to make this calamari stew for Christmas Eve this year, so I wasn't really following tradition on purpose. In our case, the reasoning wasn't that we were going to have so many heavy roasts the next day (we actually had fish on Christmas Day as well), but just that this seemed like a tasty dish similar to what we had made once before and enjoyed. There was also the added bonus that calamari is cooked for a long time in this dish, so we wouldn't run into the issue of varying preferred cooking times of meat (I generally prefer my meat cooked medium rare, some other visiting family members prefer theirs very well done).
The original recipe calls for Sambuca, an anise flavored liqueur. Since our family isn't big on anise flavor, I decided to leave it out - though I kept the fennel bulb. I also left out the final touches of parsley and fennel fronds, but that was less intentional. We served this stew over polenta and it was appreciated by all (or at least all the grown-ups).
Adapted from Simply Recipes
2 lbs cleaned calamari (squid), tubes sliced into rings and tentacles roughly chopped
4 tablespoons olive oil
1 sliced onion
1 fennel bulb, chopped
3 garlic cloves, chopped
2 tablespoons tomato paste
1 cup red wine
1 28-oz can of crushed tomatoes
Salt and pepper
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 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. Stir well to combine and serve.