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.
  • Course: Lunch


  • balsamic vinegar
  • basil leaves
  • beefsteak tomatoes cut into a total of 8
  • 1/2-inch thick slices
  • Extra Virgin Olive Oil
  • fresh mozzarella
  • ground black pepper
  • Martin's sliced potato bread
  • provolone cheese
  • Salt
  • sugar
  • unsalted butter


  1. Preheat the oven to 350°F. Line a large 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 a 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.
  4. 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.
  5. Spread the outside of each sandwich with 2 teaspoons of the butter. Heat a large 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.