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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: 392 kcal

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

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  • 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
    Declared “best grilled cheese ever” by my foodie 11 year old & “pretty darn good” by my extremely picky 8 year old. (His was modified without some of the good stuff). Anyway, I don’t know how I have lived this long without putting pesto on my grilled cheese! This is a game changer!

    1. Hey Brooke,
      Happy Sunday! I am thrilled to hear this recipe was enjoyed, thanks so much for making it! xTieghan

  2. 5 stars
    This is a winner. Both my husband and his picky 18 year old son agreed it was the best grilled cheese ever. I used my homemade sourdough bread and all fresh herbs and served it with homemade tomato soup. It’s truly the perfect winter dinner! Easy, delicious, melty and warm.

    1. Hey Kristen,
      Awesome! Thanks a lot for making this recipe. I love to hear that it was enjoyed! Happy Thursday❄️ xxT

  3. 5 stars
    So yummy, well done. I did fudge a little, used bacon instead of prosciutto, no sage at the market so I replaced with basil.
    BTW.. purchased 5 cookbooks this Christmas and passed around to my nieces.. we are all enjoying your recipes, thank you, June

    1. Hey June,
      I love to hear that this recipe was a winner, thanks so much for testing it out! Have a great week! xTieghan

    1. Hey Linda,
      Thanks a lot for trying out this recipe. I love to hear that it was enjoyed and hope you have the best week! xTieghan

  4. 5 stars
    Another genius dinner idea! This was the best grilled sandwich I have ever made! The fresh sage & parm in the butter was incredible.
    Thank you for another fantastic recipe!

  5. I am not a grilled cheese fan, but this one has converted me! The flavor, the crunch, the butter, the cheese gooeyness and the burst of tomatoes makes this the best sandwich. I have made this 3 times already – last meal before our vacation, and first one back. I craved this sandwich my whole week away! This is yet another HBH staple in our household. Thank you!

  6. 5 stars
    Delicious. Made fresh pesto to go with this. A bit time intensive — lots of ingredients for a “simple” meal, but very tasty.Prosciutto + tomato + arugula are just meant for one another.

    1. Hey Christina,
      Fantastic! Love to hear that the recipe was enjoyed, thanks bunch for making it. Have the best weekend:) xTieghan

  7. 5 stars
    Unbelievably delicious! A great melange of flavors. Perhaps a tad on the unhealthy side ;-), but the arugula and tomatoes make us feel good about eating it. Love this recipe! Told all my tennis teammates about it this morning after making it last night!

    1. Hey Connie,
      Fantastic! Love to hear that the recipe was enjoyed, thanks bunch for making it. Have the best weekend:) xTieghan

  8. 5 stars
    Oh, man! We saw this recipe and knew we had to make it! SO: a bike ride on a hot Texas morning and then a cool shower and meal prep. Easy!

    This went well with a side of red grapes and an IPA Session Ale. So delicious!! I’ll post a pic on Instagram!

    Thank you!! Love your recipes!!

    1. Hey there,
      Fantastic! Love to hear that the recipe was enjoyed, thanks bunch for making it. Have the best weekend:) xTieghan

  9. 5 stars
    Made this last night and it was delicious! My husband has already asked to have it again sometime soon. Definitely the grownup version of grilled cheese.

    1. Hey Lisa,
      Fantastic! Love to hear that the recipe was enjoyed, thanks bunch for making it. Have the best weekend:) xTieghan

  10. Just made and wow, so good! I love that this can be adapted to what you have on hand. I did make a few changes based on what I had in my fridge. I subbed the fontina and mozzarella for Havarti, the prosciutto for turkey bacon, and omitted the Parmesan and arugula. Yum!