Pork tenderloin makes the perfect dinner centerpiece when stuffed with pears and Gruyere and wrapped in crispy prosciutto.
Today’s post comes with allll the mixed emotions. There are happy memories, there are sad moments, all of which I will get more into in a moment but, for now, let’s just look at this Pear and Gruyere Stuffed Pork Tenderloin with Roasted Cippolini Onions as a nostalgic meal best shared with those you love. Because life is all too fleeting, and you need to grasp those moments when you have them.
If you read my Travel Diaries: Tuscany post, you already know that this past April the hubs and I went with both of our parents and my aunt to visit our dear friends Sergio and Stefano at their beautiful Tuscan villa. My aunt and I had been there before, but our parents had yet to experience their over-the-top hospitality and beautiful grounds.
One of the biggest regrets I had on that first trip with my aunt was that we spent every day out and about exploring, and never had the chance to stay at the Villa for a day and take a cooking class, which Sergio and Stefano specialized in. I knew that when we went back to visit this was going to be a MUST. Who doesn’t want to learn what goes into true Italian cooking?
So we spent one day on our last trip in the kitchen, learning all about how to make the fluffiest homemade gnocchi, the beefiest Bolognese and the richest tiramisu. I seriously don’t know how we did it all in the course of half of a day. But Sergio and Stefano had it down to a science, and boy did they make it all look so easy. They’d been teaching classes together for years, even traveling to the U.S. to do so, and it was oh-so-apparent in the way they took us through all of the recipes like a well-oiled machine.
We got some sad news a couple of weeks ago. Unfortunately, Sergio had lost a long struggle he had been fighting over some health issues the last couple of years. As would be expected, we were all deeply saddened by the news. At the same time, I feel so grateful that we were able to make the trip and spend so much time with him when we did. Sergio was such a gem: humble, kind, selfless and one of the friendliest people you’ll ever meet. He and Stefano had taken our crew by the hand during our trip, being the most selfless hosts while also escorting us on all of our excursions, serving as our own personal tour guides. They truly made us feel like family.
As I often do when struggling with difficult emotions, I decided the best way to both express my sympathy and honor Sergio’s memory would be through cooking. This Pear and Gruyere Stuffed Pork Tenderloin with Roasted Cippolini Onions is my own personal take on one of the (many) recipes we learned to make during their cooking class and, I have to say, I think Sergio would be proud.
It’s actually a lot more simple than it looks (or sounds,) yet is an elegant dish to serve a dinner table full of guests you care about. The version we made at the villa was filled with apples and Parmigiano, but for this version I decided to sub in one of my favorite combos: fresh pears and gruyere.
The pork tenderloin is already beautifully decadent with the filling, but becomes even more so with the light jacket of prosciutto that’s wrapped around it just before cooking.
It’s cooked completely on the stove top, but with very little hands-on work. A quick flip of the tenderloin about halfway through cooking is all you’ll need. We leave the oven open for roasting the cippolini onions, which are the perfect contrast to the Stuffed Pork Tenderloin with their sweet yet tangy glaze.
So here’s to all those we’ve loved and lost too soon, and all of the recipes we have to share the memories. Cheers to you Sergio, che tu possa riposare in pace.

Pear and Gruyere Stuffed Pork Tenderloin with Roasted Cippolini Onions
Ingredients
For the pork tenderloin:
- 1 1/2 pounds boneless pork tenderloin (or sirloin,) sliced in half and opened like a book
- 1/4 teaspoon salt
- 1/8 teaspoon pepper
- 1 pear, peeled and sliced
- 3 1/2 ounces shaved Gruyere
- 1 tablespoon butter
- 1/2 cup sherry
- 2 cups chicken broth
For the cippolini onions:
- 14 ounces peeled cippolini onions
- 3 tablespoons butter
- 4 tablespoons sugar
- 1/4 cup white vinegar
- 1/4 teaspoon salt
- 1/8 teaspoon pepper
Instructions
- Begin by pounding the pork tenderloin to a ½-inch thickness. Sprinkle with salt and pepper, then layer on the pear and Gruyere.
- Lay out the slices of prosciutto on a piece of plastic wrap so that they mimic the shape that the tenderloin has taken. For mine, I made two columns of three slices of prosciutto each, right up next to each other. Place the pork on top of the prosciutto.
- Using the plastic wrap to hold everything together, first roll up one side of the tenderloin, then the other, having the two ends of the pork meet at the top, with the prosciutto extending over that seam just a bit.
- Using a piece of butcher’s twine, make loops down the length of the tenderloin to hold everything together. I just kind of made up my method, but use whatever works best for you while losing as little of the filling as possible.
- Preheat the oven to 350 degrees Fahrenheit for the onions.
- Place a large, deep saute pan or Dutch oven on the stove over medium-high heat and melt the butter in it. Once the butter is melted and the pan is nice and hot, add the pork and brown it on all sides (about 2 minutes each side.)
- Once the pork is browned, pour in the sherry and let the alcohol evaporate off a bit, about 3 minutes. Add the chicken broth.
- Cover the pot or pan and cook for about 15 minutes.
- While the meat is cooking, prep the onions. In an 8-by-8-inch baking dish, spread out the onions in a thin layer. Cut the butter into tablespoons and drop the tablespoons evenly over the onions, followed by the sugar, white vinegar, salt and pepper. Place in the preheated 350 degree oven and cook for 30-40 minutes, or until the onions are golden brown and can be pierced easily with a fork.
- After 15 minutes, remove the lid and pour off the liquid until only about ½ cup remains. Flip the pork over and replace the lid. Cook the pork for another 15 minutes, or until cooked through.
- Transfer the pork to a serving dish and surround it with the cooked cippolini onions. Garnish with whatever fresh herbs you may have on hand!
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