Roasted Tomato Caprese Grilled Cheese

It will be months before we see tomatoes growing on vines in the Midwest, but I’m already dreaming about local heirlooms, and colorful, bright red, yellow, purple and green tomatoes.

Caprese Grilled Cheese | Making Life Sweet at

My new home in Minnesota has a small space for a box garden, so I think I’ll even be able to plant some of my own this season. Whether or not those tomatoes will be as juicy and delicious as the plump ones at the Farmers Market, I do not know. But I will make an attempt!

Tomatoes are the star of this simple grilled cheese recipe, which comes from the kitchen of How Sweet It Is blogger Jessica. Roasting the tomatoes brings out a sweet flavor that pairs perfectly with the mozzarella cheese, basil and balsamic reduction.

My fiancé and I enjoyed the whopping sandwich with a large bowl of Trader Joe’s Creamy Roasted Red Pepper Soup (my go-to box soup). For those of you who do not live near a Trader Joe’s, I am sorry… If I had the time to mail a box to you, I would! Yes. It is THAT good. Of course, you can’t go wrong with substituting for a bowl of classic tomato soup. Unless, you’re like me and suffer from tomato-overload-induced acid reflux…which in that case, I’d suggest buying another roll of Tums for that courageous combination.

Caprese Grilled Cheese | Making Life Sweet at

Roasted Tomato Caprese Grilled Cheese with Balsamic Glaze 

Author: How Sweet It Is | Serves: 2

6 tomatoes (vine or roma), sliced about 1/2 inch thick
1-2 tablespoons olive oil
1/2 teaspoon salt
1/2 teaspoon pepper
1/2 cup balsamic vinegar
3-4 ounces fresh mozzarella
12-15 basil leaves
4 slices seedy bread

1) Preheat oven to 325 degrees. Place tomatoes on a nonstick baking sheet and drizzle with olive oil, salt and pepper. Roast for 45-50 minutes. While tomatoes are roasting, add vinegar to a small saucepan and bring to a boil. Reduce to a very low simmer and cook for 10-15 minutes, until liquid reduces by about half and is slightly syrupy. Remove from heat, pour vinegar in a bowl or glass to pour, and let sit.

2) Once tomatoes are finished, heat a large griddle or skillet over medium heat. Brush the outsides of each slice of bread with olive oil, then place mozzarella on one slide, followed by tomatoes, basil (feel free to shred it if you’d like), more tomatoes and more mozzarella. Cook until cheese is melty and each side is golden, about 5 minutes per side. Serve immediately drizzle with balsamic.