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Calera wines on a board while outdoor cooking

Chicken Cacciatore with Heirloom Tomatoes and Fennel

Chicken Cacciatore

Yield: 4-6 servings
Prep: 20 minutes | Cook: 1 Hour
Total Time: 1 hour and 20 minutes

This classic cacciatore celebrates the seasonality of heirloom tomatoes rather than opting for a jar of tomato sauce. Add in a side of grains or simple pasta to make it a meal on its own.


  • ¼ cup flour, seasoned with salt and pepper
  • 2 tablespoons extra virgin olive oil
  • 6 chicken thighs, with bones and skin
  • 1 red bell pepper, sliced
  • 6 cremini or white mushrooms, sliced
  • 1 small bulb of fennel, sliced, plus fennel tops for garnish
  • ½ yellow onion, sliced
  • 2 cloves of garlic, sliced
  • Salt
  • 3 large heirloom tomatoes
  • ½ cup red wine for cooking
  • 1, 4oz can tomato paste
  • 1 bunch of thyme
  • 1 cup of pitted kalamata olives, roughly chopped/crushed


  1. Begin by dusting the chicken thighs with the seasoned flour. Pat off any excess flour and set the chicken aside.
  2. Heat a large dutch oven with a lid up to medium high heat with two tablespoons olive oil. When the oil is hot, brown the chicken thighs on both sides, then set aside. Drain off any excess fat, then add the sliced vegetables to the dutch oven. Season with a pinch of salt and cook, stirring occasionally, for 2-3 minutes or until just beginning to brown.
  3. Roughly chop the heirloom tomatoes into big chunks and add to the pot with the red wine and tomato paste. Continue cooking and stirring until the tomato paste is incorporated. Reduce the heat to medium low and replace the chicken thighs - they should be at least halfway submerged. Add a bunch of thyme and place the lid on the dutch oven and allow the chicken and sauce to simmer for forty minutes to an hour, or until chicken is fall off the bone tender.
  4. Allow the chicken to cool a little in the sauce before stirring in the kalamata olives and transferring to a serving dish. Finish the dish with extra fennel greens or fresh herbs and a drizzle of extra virgin olive oil.


Take a look at our recommended pairing below.


Pairing Recommendations - Red Wines

Pairing Recommendation

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