Thick slices of mozzarella, sweet roasted tomatoes, fresh baby spinach, and a smear of pesto get stuffed between two pieces of crusty bread and cooked until gooey and oozing.

Roasted Tomato Caprese Grilled Cheese Sandwich

April is dedicated to melted, gooey cheese stuffed between two pieces of crusty bread that have been buttered and toasted to perfection.

It’s National Grilled Cheese Month–also known as the best month ever!

The #SundaySupper team has partnered with Gallo Family Vineyards to help celebrate this glorious cheese-filled month with cheese’s best friend: wine. It’s a match made in foodie heaven, and I’m excited to share this roasted tomato caprese grilled cheese sandwich in honor of such a delicious occasion.

Gallo Family Wine

Gallo let us have free range of their wine selection this month. They have so many wonderful wines to choose from, that I had a difficult time making my selection. Mmm, all of them?

I finally decided on their crisp, slightly fruity Pinot Grigio and their bold, berry-infused Pinot Noir to pair with my grilled cheese sammie. Different strokes for different folks, right? While I prefer a fruity white, others may prefer a rich red, so I chose one from each wine grouping.

Vine-Ripened Tomatoes

Cheese and wine are in a committed relationship that will never die or go out of style–it’s a timeless classic. There’s no wrong answer when it comes to pairing wine with cheese. Any selection you make is the right selection and will pair perfectly and taste absolutely delicious. That’s the glorious thing about wine and cheese–anything goes!

Gallo Family Wine

This roasted tomato caprese grilled cheese has quickly become one of my favorite sammies. It’s easy, yet impressive. You can dress it up for a casual dinner party or make it on a busy weeknight.

If you’ve never roasted tomatoes, I highly recommend giving it a try. The tomato flavor concentrates as the tomatoes back, creating a sweet, juicy, roasted-to-perfection tomato. Roasting tomatoes is a breeze. Place your tomatoes (I used campari) on a sheet pan and drizzle with olive oil. Sprinkle them with a little kosher salt and pepper. Place them in a 400 degree F. oven to bake for 40 minutes. If you’re using a smaller tomato, like grape or cherry, reduce the cooking time to 30 minutes.

Vine-Ripened Tomatoes

Because we’re using roasted tomatoes for this recipe, choosing the perfect loaf of crusty bread is a must. I used thick, chewy ciabatta bread for this recipe. I do not recommend using a flimsy loaf bread, such as white, in this case because of the juiciness of the tomatoes. You want a loaf of bread that can soak up the juice without losing its integrity and falling apart.

Roasted Tomato Caprese Grilled Cheese Sandwich

This sammie is piled high with thick slices of mozzarella, sweet roasted tomatoes, fresh baby spinach, and a smear of pesto. The result is a deliciously gooey mess.

Gallo Family Vineyards

Find a Gallo Family Vineyards retailer near you with their store locator. To receive updates, follow Gallo on Facebook, Twitter, Instagram, and You Tube. Visit Gallo’s Grilled Cheese blog post and the Cooking with Wine Pinterest board for more wine pairing suggestions and recipe inspiration.

Roasted Tomato Caprese Grilled Cheese

Thick slices of mozzarella, sweet roasted tomatoes, fresh baby spinach, and a smear of pesto get stuffed between two pieces of crusty bread and cooked until gooey and oozing.


  • 1 pound campari tomatoes
  • 1 tablespoon extra-virgin olive oil
  • 2 pieces ciabatta bread, sliced in half
  • 8 ounces fresh mozzarella, cut into 1/2-inch slices
  • handful baby spinich
  • 2 tablespoons pesto
  • salt and pepper


  1. Preheat oven to 400 degrees F. Line a baking sheet with parchment. 
  2. Place the tomatoes on the baking sheet and drizzle with olive olive. Sprinkle with a generous pinch of kosher salt and pepper. Bake for 40 minutes, or until the tomatoes are wilted and the skin is wrinkled. Allow the tomatoes to cool slightly. 
  3. Heat a large skillet over medium-low heat. 
  4. Smear 1/2 tablespoon of pesto on each slice of ciabatta bread. Place a few slices of mozzarella on one half of the ciabatta roll. Top with roasted tomatoes and spinach. Place the other half of the roll on top. 
  5. Cook on each side for 3-5 minutes, or until golden brown.
  6. Slice in half and serve immedieately.  
  1. You can roast the tomatoes up to 3 days ahead of time. Store the cooled tomatoes in an airtight containter and place in the refrigerator until you’re ready to use. 
  2. If you’re using a smaller tomato, such a grape or cherry, reduce the roasting time to 30 minutes. 
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Check out the other grilled cheese recipes:

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Disclosure: Compensation was provided by Gallo Family Vineyards via Sunday Supper, LLC. The opinions expressed herein are those of the author, and are not indicative of the opinions or positions of Gallo Family Vineyards.