Grilled Cheese Caprese with Balsamic Syrup Drizzle

By Marge Perry & David Bonom

This is what happens when a simple grilled cheese sandwich grows up and learns the art of self-expression. The deep, rich umami (savory) flavor of the roast tomato provide the perfect foil for the creamy, rich cheese and the surprising tangy sweetness of the balsamic syrup. 

  • Yield: 4 servings
  • Course: Lunch

All you need for this recipe and more...


2 large beefsteak tomatoes cut into a total of 8, 1/2-inch thick slices

1 tablespoon extra virgin olive oil

1/4 teaspoon salt

1/8 teaspoon ground black pepper

1/3 cup balsamic vinegar

1 tablespoon sugar

8 slices Martin’s sliced potato bread

8 ounces fresh mozzarella, sliced

16 large basil leaves

8 slices provolone cheese

8 teaspoons unsalted butter, softened


1. Preheat the oven to 350°F. Line a large Anolon® Advanced Bronze baking sheet with parchment paper. 

2. Brush the tomato slices with the oil and arrange them in a single layer on the baking sheet. Season with salt and pepper.  Roast the tomatoes until they are very soft and just hold their shape, about 1 hour. Remove from the oven. 

3. Meanwhile, combine the vinegar and sugar in an Anolon® Authority 1.5-Quart Saucepan. Bring the mixture to a simmer over medium heat, stirring occasionally. Simmer until the liquid is reduced to a syrupy consistency, about 10-12 minutes. 

3. Place 4 slices of the bread on a work surface. Top each with 2 ounces of the mozzarella. Place 2 tomato slices on top, then 4 basil leaves, followed by 2 slices of provolone cheese. Place the remaining slice of bread on each sandwich. 

4. Spread the outside of each sandwich with 2 teaspoons of the butter. Heat a large Anolon® Authority 12.5-Inch nonstick skillet over medium heat. Add 2 sandwiches, cover the pan with a lid or large piece of aluminum foil. Cook until the sandwiches are golden brown and the cheese has melted, about 3-4 minutes per side. Repeat with the remaining sandwiches. To serve, cut each sandwich in half diagonally and drizzle with balsamic syrup.