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Crispy Prosciutto, Sage Pesto, and Tomato Grilled Cheese…all the flavors we love in a bowl of really good tomato soup…but in the form of grilled cheese. Summer tomatoes and crispy prosciutto layered between two slices of bread with fresh sage, basil pesto, melty fontina, and mozzarella cheese. This sandwich is coated in parmesan sage butter, then pan-fried until the cheese is melty and the bread is crisp. It’s savory, herby, and heavy on the cheese…the most perfect summer grilled cheese…any day of the week.

Crispy Prosciutto, Sage Pesto, and Tomato Grilled Cheese |

We’ve got Monday grilled cheese sandwiches to keep things easy, casual, and delicious…plus comforting too. I mentioned this yesterday, but our weather has shifted and there is most definitely a slight chill in the air.

I’m not ready for fall food just yet. But I’m starting to lean into the cozier end-of-summer recipes…which are always some of my favorites.

This grilled cheese is just that…summery, but comforting. I’ve told this story before, but as a kid, my grilled cheese sandwiches consisted of whatever bread we had laying around the kitchen, plus cheese, and butter. Three ingredients that can do no wrong. My dad would make my brothers and me grilled cheese on nights when he didn’t have much else in the kitchen. He was always heavy on the sharp cheddar. He made them extra buttery on soft whole wheat bread.

Nothing special, but always delicious.

Crispy Prosciutto, Sage Pesto, and Tomato Grilled Cheese |

The idea for today’s grilled cheese came from the garden. We have so much fresh baby arugula right now and so many herbs it’s insane. I really wanted to work the arugula into a recipe along with some warming sage. A grilled cheese sounded just too perfect.

Crispy Prosciutto, Sage Pesto, and Tomato Grilled Cheese |

The details

Start out by seasoning the tomatoes. Find some delicious ones, preferably heirloom, and then salt them. This helps to draw out any excess moisture the tomatoes may have. This step is key and ensures that your grilled cheese sandwich will never become soggy.

While the tomatoes are sitting, crisp up the prosciutto in a skillet. You could skip this step, but we LOVE salty, crispy prosciutto…so delicious!

Crispy Prosciutto, Sage Pesto, and Tomato Grilled Cheese |


When you have the tomatoes salted and the prosciutto crisp, it’s assemble time.

Mix the butter with grated parmesan and fresh sage, then slather it over the bread. Trust me, you can’t skip this. It makes each grilled cheese feel extra special.

Now layer up the sandwiches with fontina cheese, tomatoes, pesto, arugula, and prosciutto, then add a handful of melty mozzarella.

Crispy Prosciutto, Sage Pesto, and Tomato Grilled Cheese |

Next, simply pan fry the sandwich with olive oil or even just another pat of butter.

Five minutes later you’ll have the best summery grilled cheese. The cheese on the inside becomes that melty goodness we love so much. While the outside of the bread becomes crisp from the parmesan, which is literally pan-fried into the bread.

So so delicious, and even kind of pretty too!

It’s the crispy prosciutto, sage, spicy arugula, and pesto that really work so well together. And that tomato, well it just makes things even more delicious.

Make this tonight as an easy summer dinner, but keep it in your back-pocket for busy nights throughout the fall.

Crispy Prosciutto, Sage Pesto, and Tomato Grilled Cheese |

Looking for other grilled cheese recipes? Here are a few ideas: 

French Onion and Apple Grilled Cheese

Everything Cheddar Tomato Bacon Grilled Cheese

Breakfast Grilled Cheese

Lastly, if you make this Crispy Prosciutto, Sage Pesto, and Tomato Grilled Cheese, be sure to leave a comment and/or give this recipe a rating! Above all, I love to hear from you guys and always do my best to respond to each and every comment. And of course, if you do make this recipe, don’t forget to tag me on Instagram! Looking through the photos of recipes you all have made is my favorite!

Crispy Prosciutto, Sage Pesto, and Tomato Grilled Cheese

Prep Time 15 minutes
Cook Time 10 minutes
Total Time 25 minutes
Servings: 2 sandwiches
Calories Per Serving: 952 kcal

Nutritional information is only an estimate. The accuracy of the nutritional information for any recipe on this site is not guaranteed.



  • 1. Arrange the tomatoes on a cutting board and sprinkle with salt and pepper. Let sit 15 minutes to draw out excess moisture.
    2. In a large skillet set over medium heat, cook the prosciutto until crisp, about two minutes per side. Remove from the skillet.
    3. In a bowl, combine the butter, parmesan, and one tablespoon sage.
    4. Brush the outside of each slice of bread with the sage butter. On the inside of half of the slices of bread, evenly layer half of the cheese, the tomatoes, pesto, a sprinkle of chopped sage, arugula, prosciutto, and the remaining cheese. Add the top piece of bread.
    5. Heat 1-2 tablespoons olive oil or butter in a large skillet over medium heat. Place the sandwiches in the skillet and cook until golden on each side, about 3-5 minutes per side. EAT and ENJOY!
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Crispy Prosciutto, Sage Pesto, and Tomato Grilled Cheese |

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  1. 5 stars
    I’m an intern at a hospital to become a dietitian and one of my projects was to find a recipe, standardize it, and sell it in the hospital’s cafeteria. I knew to look on Half-Baked Harvest for ideas because I love your recipes! To fit within budget, I followed this recipe the same but swapped out the crispy prosciutto for bacon and it was still delicious. I was able to sell almost 100 of these sandwiches within 2 hours, needless to say this recipe was a hit!! Thank you for your recipe creativity!

  2. 5 stars
    I was looking for a recipe to use up some sage I had leftover and I already had the other ingredients on hand. This was so good!

    1. Hi Natalie,
      Thanks for your comment and trying this recipe! I am so glad it turned out well for you! Have a great day:)

  3. 5 stars
    I’ve made this numerous times, it’s so amazing. Had some leftover fresh mozzarella so used that this time, sliced thin. It was fantastic.

  4. This was SO good! We loved it! I will be making this over and over again. Now to try the Everything cheddar tomato bacon grilled cheese! Can’t wait!

    1. Hey Julie,
      Wonderful!! Thanks so much for making this recipe and sharing your comment, so glad to hear it was a winner! xT

  5. 5 stars
    Absolutely delicious! A huge hit with my entire family. It helps to use two spatulas when flipping the sandwich so all the wonderful ingredients stay inside.

    1. Hey Lezah,
      Awesome!!🌼 I love to hear that this recipe turned out well for you and appreciate you giving it a try! xT

  6. 5 stars
    Made it today for a late lunch. DELICIOUS! I might go lighter on the pesto next time, but add extra crispy prosciutto! Thank you for the wonderful recipes!!!

    1. Hey Marlene,
      Happy Friday!! I appreciate you making this recipe and your comment, so glad to hear it was delish! xx

    1. Hey Djienne,
      Happy Sunday!!❄️ I love to hear that this recipe was enjoyed, thanks so much for trying it out and sharing your feedback! xx

    1. And… I did not need to add butter or oil to the skillet. Buttering the bread provided plenty of butter for grilling.

  7. 4 stars
    First I want to say how yummy this sandwich turned out. I did have to substitute a couple of ingredients to what I had on hand. I used spinach instead of the arugula and bacon instead of the prosciutto. I also added a little bit of shredded rotisserie chicken to make it substantial enough for dinner (per hubby’s request). Now, that being said, the sandwich was very greasy from the butter, the pesto, and the oil used for cooking. The extra oil/butter is unnecessary for cooking due to the compound butter spread already on the sandwich. I will definitely make again with a little less pesto and will definitely not use any oil/butter in the pan.

    1. Hey Maria,
      I appreciate you making this recipe and sharing your review, I am so glad it was enjoyed! Have a great day:)

  8. Another great way to make “Crispy Prochutto” is like this:

    400 degree oven

    On cookie sheet w/grid cooling rack on top, Lay all your Prochutto in a single layer on top of grid.

    Cook at 400 degrees for 8 minutes.