Red Wine Marinated Flank Steak filled with Prosciutto, Fontina, and Basil

That’s quite the fancy recipe title, isn’t it?! There aren’t very many fancy recipes on Sew You Think You Can Cook because we’re just not that fancy of people. And fancy usually takes way more time and effort than I have patience for.

So why am I sharing such a fancy dish with you today?

Because today is the 5th anniversary of my marriage to a man who makes me laugh (don’t tell him I said that), makes me smile, and makes my dreams come true. photography by Cher Hanna

Photography by Cher Hanna

A little over 5 years ago we thought that today we’d be laying in a hot tub looking at the mountains and ocean in St. Lucia. It’s amazing how much happens in 5 short years! Instead of taking that anniversary trip we are expecting our second child and at a point in my husband’s career where taking a long vacation just isn’t possible. So get ready St. Lucia, we’re coming for you in 5 years! (Grandparents, clear your calendars.)

We aren’t doing anything tonight either. Similarly to last year, Stuart signed up for a race this weekend. Although this one is only 12ish miles and not 30 hours in the woods. Also – family is coming into town to attend our son’s baptism on Sunday (finally!).

Red Wine Marinated Flank Steak
filled with Prosciutto, Fontina, and Basil

Ingredients:

  • 3 shallots, diced
  • 3/4 C Cabernet red wine
  • 3 tbsp olive oil
  • 1 1/2 lb flank steak, butterflied
  • 4 oz thinly sliced prosciutto
  • 4 oz thinly sliced fontina cheese
  • approximately 14 fresh basil leaves

Steps:

  1. Whisk together shallots, wine, and olive oil. Place in a large casserole dish (or a resealable plastic bag). Add the steak and marinate in the fridge a minimum of 4 hours.
  2. Remove steak from the marinade and dry with paper towels. Lay cut side up and season with S+P. Cover with prosciutto, fontina, and basil leaves. Roll the steak around the filling on the long side. Tie with kitchen string in 4-5 places.
  3. Brush the outside of the roulade with a little bit of olive oil and season with S+P.
  4. Grill the steak over medium-high heat on all sides for a total of 10 minutes. Move the steak away from direct heat and cook another 20 minutes, or until an internal temperature of 125 (or greater) is reached depending on your preference.
  5. Cover the roulade with foil and allow to rest for 5 minutes before slicing. Serve with Cabernet-Shallot Reduction (recipe below).

Cabernet-Shallot Reduction

Ingredients:

  • 1 tbsp olive oil
  • 1 1/2 shallots, diced
  • 1 2/3 C Cabernet red wine
  • 1/2 tsp black peppercorns
  • 1 tbsp honey

Steps:

  1. In a small saucepan over medium-high heat saute the shallots in olive oil until tender. Add the wine and peppercorns. Bring to a boil and cook 15 minutes, or until the sauce has reduced to 1/2 C. Strain. Stir in the honey and season to taste with salt.

*These recipes are adapted from Bobby Flay’s Grill It!*

Red Wine Marinated Flank Steak filled with Prosciutto, Fontina, and Basil | Sew You Think You Can Cook

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9 thoughts on “Red Wine Marinated Flank Steak filled with Prosciutto, Fontina, and Basil

  1. Happy anniversary, Lauren! Your wedding photos are gorgeous! Life doesn’t always turn out the way we planned it but it’s all good. That is one tasty steak dish and the perfect way to celebrate.

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