Grilled Cheese Sandwiches with Spicy Grapefruit Salad

Grilled Cheese Sandwiches with Spicy Grapefruit Salad
  • Cook Time
  • Prep Time
  • 4Servings


  • 2 grapefruits, cut into segments, juice reserved
  • 2 scallions, chopped
  • 1 jalapeno chile, seeded and finely chopped
  • 3 tablespoons extra-virgin olive oil, plus more for brushing
  • Salt and pepper
  • 1 fennel bulb, cored and thinly sliced
  • 8 1/2-inch slices round sourdough bread
  • 8 deli slices Swiss cheese
  • 2 cups arugula


In a medium bowl, combine the grapefruit and all but 2 tablespoons of the juice, the scallions, jalapeno and 2 tablespoons olive oil; season with salt and pepper.

Preheat an outdoor grill or a grill pan to medium-high. In a medium bowl, toss the fennel with 1 tablespoon of the olive oil and the remaining 2 tablespoons grapefruit juice; season with salt and pepper.

Arrange the bread slices on a work surface; top each with a slice of cheese, one-quarter of the fennel, one-quarter of the arugula and a second slice of cheese. Cover with the remaining bread slices.

Brush one side of the sandwiches with olive oil. Place oil side down on the grill; brush the tops with olive oil. Grill, turning once, until the cheese is melted and grill marks appear, about 7 minutes. Serve with the spicy grapefruit salad.