Caramelized Fennel with Tomato, Olive and Orange

The other day I was in the mood to cook something unfamiliar. It was a Wednesday, nothing interesting happened on Monday or Tuesday and I needed a little excitement. The answer: dinner party.  As of September 1st, all my friends moved to opposite corners of Boston. Literally, opposite: Brighton, Mission Hill, North Quincy, Somerville, Milton, and Charlestown. Consequently we haven’t seen as much of each other, and it needed to happen. A dinner party was the perfect mini-reunion to meet back up and chat about all these new living situations and what not.

Now for the food… my brother is a chef, and he’s really good. Tom can take any number of random ingredients and come up with something delicious and Food-Network worthy. That’s why I called him for a dinner party idea. All he had to say was “caramelized fennel” and I was set. I have never cooked with fennel or caramelized anything. Meesh: 1, mid-week slump: 0.

Fennel is intimidating:

Here is Tom’s original recipe for Caramelized Fennel with Tomato, Olive and Orange (if you see him on Top Chef, you saw it here first!):


  • 1 pint cherry tomatoes
  • 1 head fennel
  • 1 cup kalamata olives, pitted and quartered
  • 1 orange, for juice and zest
  • ½ cup basil leaves
  • 3 tablespoons balsamic vinegar
  • 1.5 cups olive oil
  • Salt
  • Pepper
  • Thyme


For the Tomatoes:

  • Preheat oven to 400
  • Toss whole grape tomatoes with balsamic and lightly coat with oil, mix in salt, pepper and thyme
  • Roast tomatoes in oven until they get sufficient color on them
  • Remove from oven and set aside

For the Fennel:

  • Remove the tops of the fennel and discard
  • Cut the head on fennel and cut into 8 equal sized wedges with the core still intact so that they maintain their shape
  • Heat oil in a pan to medium high heat (try to gauge the amount of oil so it will reach ¾ of the way up the fennel – it will not cook evenly with too little oil!)
  • Add the fennel and cook until it starts to brown, then squeeze some of the orange juice over the fennel wedges
  • Turn the fennel over and repeat on the other side, cook until you see the fennel caramelizing from the sugar of the orange, it creates a crispy brown surface on the fennel.
  • Remove fennel from pan, place on paper towel to drain oil, and sprinkle with salt immediately.

To Finish:

  • In a bowl mix tomatoes, olives , orange zest, and the torn basil leaves, and mix that together
  • Add fennel when serving (it will be too delicate to mix with the tomatoes)
  • Rejoice


The flavors mix perfectly together, the bitterness of the olive and the sweetness of the orange create a really nice blend. The orange also balances out the licorice flavor of the fennel. Do I even have to mention the balsamic? Fennel is easy to work with and tastes great, don’t be scared of it!


  • Squeeze a lot of orange juice on the fennel to caramelize it, be really generous with this. I didn’t get this right until my third batch, but that third batch was money.
  • Don’t forget the salt when you take the fennel out of the pan.
  • Don’t be as generous with the orange zest. Orange zest has a really strong flavor that was a tad bit overbearing.
  • Make sure the oil is hot when you add the fennel to the pan.
  • Can be served with chicken, steak or fish.


This entry was posted in Dining In, Entree, Recipes, Vegetarian and tagged , , , , , , , , , . Bookmark the permalink.

2 Responses to Caramelized Fennel with Tomato, Olive and Orange

  1. Pingback: The Long and the Shortrib Stroganoff | Just Add Cheese!

  2. Pingback: Winter Salad | Fennel, Olive and Orange | Just Add Cheese!

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