Trim and remove all silver skin and fat from the beef. Rub meat with the olive oil and then splash with sherry. Continuing to rub beef, then sprinkle the steak seasoning all over the meat. Cover beef on all sides with the fresh herbs, rubbing to coat.
Place meat in a shallow pan and allow to rest for 30 minutes. Turn and pat beef with the marinade that has collected in the pan. Allow to rest for an additional 30 minutes.
Heat the grill to 500 degrees F.
With an 8-inch knife, carefully pierce the meat in the center of 1 end. Cut a hole through that side as far into the fillet as the knife will allow. Turn to the other end and repeat this process, until the hole extends all the way through the fillet. Open the hole like a tunnel, being careful not to break through to the outside of the fillet. Using only small amounts at a time, stuff the cooled Spinach Stuffing into the opening from 1 end to the other.
Reduce grill temperature to 400 degrees F.
Place the stuffed beef tenderloin on the grill and, turning every 5 to 7 minutes to avoid burning the herbs, cook to an internal temperature of 110 to 120 degrees F. Cooking time for a medium-rare tenderloin is approximately 20 minutes.
Once the tenderloin is cooked to your liking and removed from the grill, allow to rest for 10 minutes. Slice into 1/2 to 1-inch medallions. If desired, serve on a bed of roasted marinated red and yellow peppers with a green salad of your choice tossed in Maple Balsamic Vinaigrette.
Heat oil in a saute pan over high heat. Add frozen spinach, garlic, and red pepper flakes, and saute over high heat until the spinach has lost its moisture and is heated through, approximately 3 to 5 minutes. Add sherry and cook for 2 minutes. Add bread crumbs and Romano cheese. Cook for 1 to 2 minutes, until the ingredients combine into a soft-textured stuffing. If the stuffing seems too dry, add some additional sherry. If the stuffing seems too wet, add more bread crumbs.
Remove from heat and add salt and pepper, to taste. Add all fresh herbs and mix gently. Allow to cool before stuffing into tenderloin.
Maple Balsamic Vinaigrette:
Mix the mustard with the vinegars. Add the oil and combine well. Add all the dry seasonings and mix together. Add the maple syrup and stir until combined.
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