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Roasted Garlic Caprese Grilled Cheese. Slow roasted summer tomatoes and sweet roasted garlic, sandwiched between slices of sourdough bread with fresh basil pesto and mozzarella cheese. Then pan-fried until the cheese is melty and the bread is crisp. Tis’ a true end-of-summer delight. 

Roasted Garlic Caprese Grilled Cheese |

Is there anything better than a really good grilled cheese? To me, it’s just feel-good classic comfort food. As a kid, my grilled cheese sandwiches consisted of whatever bread we had laying around the kitchen, cheese, and butter. My dad kept it simple, but they’d never disappoint. 

It’s truly hard to beat a melted cheddar sandwiched between 2 slices of buttered bread. 

However, as much as I love the classic simple grilled cheese, I’m also all about making grilled cheese the “fancy” way. Though I don’t really consider this recipe fancy – just totally delicious. 

Roasted Garlic Caprese Grilled Cheese |

Here are the details

Aside from the time needed to roast the tomatoes, this is almost as easy as the 3-ingredient grilled cheese my dad would make. Almost. 

First things first, the tomatoes. Find some really good ones with really nice color. Mine were on their last leg, which was honestly perfect for roasting. 

Roasted Garlic Caprese Grilled Cheese |

Then grab a head of garlic and smash it down. Toss the cloves onto a baking sheet with the tomato slices and season everything generously with salt and pepper. Next, roast away until the tomatoes start to char and become even sweeter than before. 

At the same time, the garlic roasts and turns into a buttery golden clove that can easily be smashed further down into a paste. 

When the tomatoes are finished, I further mash the cloves of garlic. Then I mix the tomatoes and garlic with basil pesto. 

Now all that’s left to do is assemble. 

Roasted Garlic Caprese Grilled Cheese |

My secret 

Fig preserves, which are certainly not traditional in a Caprese. But the jam adds a sweetness that really balances out the richness of the melted cheese and the savory flavors from the basil. 

It’s the layers of flavor that really make this Caprese grilled cheese stand out.

Roasted Garlic Caprese Grilled Cheese |

Layer the jam with mozzarella cheese, roasted tomato slices, garlic pesto, and then more cheese. Pan-fry the sandwiches with butter until golden and crisp. The cheese on the inside becomes that melty goodness we love so much. 

Five minutes later you’ll have the best summery grilled cheese, so so delicious! A wonderful way to use up the end-of-summer tomatoes and herbs and celebrate these precious last few weeks of summer. 

Roasted Garlic Caprese Grilled Cheese |

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

Crispy Prosciutto, Sage Pesto, and Tomato Grilled Cheese

Everything Cheddar Tomato Bacon Grilled Cheese

French Onion and Apple Grilled Cheese

Breakfast Grilled Cheese

Lastly, if you make this, Roasted Garlic Caprese 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!

Roasted Garlic Caprese Grilled Cheese

Prep Time 15 minutes
Cook Time 45 minutes
Total Time 1 hour
Servings: 2 grilled cheese
Calories Per Serving: 781 kcal

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



  • 1. Preheat oven to 425° F.
    2. Arrange the tomato slices on a parchment-lined baking sheet. Scatter the smashed garlic cloves around the tomatoes. Drizzle everything with olive oil and season with salt pepper, and chili flakes. Bake 20-25 minutes, until tomatoes are deeply roasted.
    3. Remove the garlic from the pan and pop the cloves out of the skin. Mash the cloves with a fork into a paste. Mix the roasted garlic with the basil pesto.
    4. Brush the outside of each slice of bread with butter. On the inside of half of the slices of bread, spread with fig preserves. Evenly layer the cheeses, the tomatoes, pesto, and the remaining cheese. Add the top piece of bread.
    5. Melt 1-2 tablespoons 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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  1. 5 stars
    This was excellent! I love the addition of the roasted garlic to the pesto. Crazy delicious! I’d recommend being careful with the fig, if you use it. It’s delicious, but use it sparingly or if it can be a little overbearing from the sweetness.
    Someone mentioned the idea to try balsamic and I’m very intrigued to try that next time.

    1. Hi Jim,
      Happy Wednesday! Thanks so much for giving this recipe a try, I am thrilled to hear that it was a winner! xTieghan

  2. 4 stars
    Loved the flavors of the sandwich, and will be making again. For some reason my sandwich came out really oily. Is there a way to prevent that? The sandwich came out really flat I think it might of been because of all the oils from the cheese and butter.

    1. Hi Daisy,
      Thanks for giving the recipe a try! Was there anything you adjusted? I would say that grilled cheese sandwiches are usually on the greasy side:) xx

  3. 5 stars
    These are on constant menu rotation since our tomato plant is in overdrive right now! So delicious! Hubby wants me to add prosciutto next time, so we will give it a try!
    Thanks for another amazing recipe!

    1. Hey Shannon,
      Happy Wednesday! Thanks so much for making this recipe so often, I am thrilled to hear that it is always a winner! xTieghan

    1. Hi Katie,
      Amazing!! I love to hear that this recipe was enjoyed, thanks so much for making it! Have a great weekend! xTieghan

  4. 5 stars
    5+ stars! Combination of flavors is perfect…and SO good. Added bacon to hubby’s sandwich at his request, but truly this sandwich is incredible as is. Thank you!

    1. Hey Jill,
      Fantastic! I truly appreciate you making this recipe and sharing your feedback, I am so glad it was tasty for you! xT

    1. Hi Laura,
      Fantastic! I truly appreciate you making this recipe and sharing your feedback, I am so glad it was tasty for you! xT

  5. 5 stars
    Just made for the second time! This time to share with my momma. Best sandwich I have EVER eaten.
    Thank YOU Tieghan!

    1. 5 stars
      I made this creation tonight. What a delicious sandwich! I can’t wait to make it again. Thank you so much for the recipe Tieghan!

  6. 5 stars
    Definitely making this one again.. the flavors perfectly complement each other. Made with fresh heirloom tomatoes from the garden.. delicious!!

    1. Hi Alexandra,
      Perfect! I appreciate you making this recipe and sharing your review, I love to hear that it was a hit! xxT

    1. Hi Bethany,
      Happy Labor Day! Thanks so much for making this recipe and sharing your feedback! So glad it was enjoyed:)

    1. Hi Heather,
      You will sprinkle those throughout the sandwiches with the cheese and tomatoes. I hope you love this recipe, please let me know if you give it a try! xTieghan

  7. You’ve taken a humble grilled cheese and turned it into a masterpiece.
    My husband and I enjoyed it today for lunch with farm fresh heirloom tomatoes.
    It was amazing. I’m going to the farm market tomorrow for more tomatoes so we can have another later in the week. Thanks for the recipe!