Caprese Grilled Cheese Sandwiches (Gluten-Free)

This entry is part 52 of 54 in the series Food Network

Caprese Grilled Cheese Sandwiches; 2014 Jane Bonacci, The Heritage Cook

Most of us grew up eating grilled cheese sandwiches made with American cheese and white bread. There was nothing better with a bowl of tomato soup on cold days. But, now that I’m an adult and American cheese just doesn’t cut it anymore. These days I prefer something more flavorful such as sharp Cheddar cheese, Havarti or Gouda.

Lately, I’ve been craving grilled cheese sandwiches, but it’s summer and we’ve had temperatures over 100 degrees many times. The farmers’ markets and grocers are piled high with heirloom tomatoes and that gave me an idea …. what if I added tomatoes to the grilled cheese? Hmmm, that has possibilities! Today’s Food Network #SummerSoiree theme is “BBQ anything” and I kind of took that literally. Instead of the typical steak, chicken, burgers or dogs, I decided to go vegetarian.

My favorite summer salad is the Italian classic Caprese. It is made with three ingredients: ripe tomatoes (red), fresh mozzarella (white) and basil (green) – the colors of the Italian flag. This combination shows up on menus in many forms. Sometimes you’ll see skewers with cherry tomatoes and bocconcini (mini mozzarella balls) as appetizers; the classic Margherita pizza; or my favorite – the salad made with layered concentric circles of sliced tomatoes, mozzarella with fresh basil and a drizzle  of olive oil.

Caprese Grilled Cheese Sandwiches; 2014 Jane Bonacci, The Heritage Cook

Now, how could I figure out a way to turn my favorite salad into a sandwich and cook it outdoors for a fun twist? I love challenges, don’t you? The concept is the same, but the ingredients and technique have changed. No problem!

If you can find heirloom tomatoes at your market, they are worth the cost for dishes like this where tomatoes really shine. Make sure you slice them fairly thick so they will hold up to the grilling and flipping. Plum tomatoes are meatier than other types, and perfect for this recipe. Pat them dry with paper towels to keep the bread from getting soggy.

Caprese Grilled Cheese Sandwiches; 2014 Jane Bonacci, The Heritage Cook

Assemble the ingredients for a healthy and delicious meal!

Mozzarella is very mild and I knew it didn’t have enough of a “cheesy” flavor to satisfy our impression of what a grilled cheese sandwich should taste like. Adding some white Cheddar boosts the cheese flavor while maintaining the white color. If all you have is yellow Cheddar at home, that’s fine. The combination of the two cheeses gave these sandwiches a creamy cheesiness without screaming, “I’m made with Cheddar!” Instead of just throwing a slab of Cheddar on the bread, grate it first. Grating allows it to melt easier, avoiding the risk of overcooking or burning the bread.

I love the look of whole basil leaves in dishes, but I hate getting an entire leaf in one bite. It overwhelms the other flavors. To get around this, cut the basil into tiny slices. You can stack the basil leaves and then roll them into a “cigar” shape and slice them thinly, crosswise, into ribbons. This is a classic technique called “chiffonade.” Then sprinkle these ribbons across the entire surface of the sandwich so each bite has just the right amount of basil.

Caprese Grilled Cheese Sandwiches; 2014 Jane Bonacci, The Heritage Cook

Glorious Basil

Alright, all the ingredients are assembled and prepped. Now it’s time to get grilling! You don’t want to cook this over a hot fire or you will burn the bread before the cheese has a chance to melt. The secret is a medium fire and moving the sandwiches to a cooler area if they start to get too dark too quickly. Keep an eye on them and do not walk away from the grill.

The touch of smoke was delightful with the Caprese flavors, similar to a wood-fired pizza, adding a nuance that really enhanced the sandwich. I loved that I could make a hot lunch without heating the kitchen. Everyone loved the new spin on our childhood favorite.

So, the next time you are looking for something different for your outdoor entertaining, try these upscale grilled cheese sandwiches. While your guests will always treasure their memories of American cheese and tomato soup, I bet they will agree that this combination is a wonderful alternative!

Caprese Grilled Cheese Sandwiches; 2014 Jane Bonacci, The Heritage Cook

Jane’s Tips and Hints:

Before the cheese has melted on both sides, these sandwiches tend to want to slide around. Using a spatula, slip it under each sandwich and hold the top with your other hand. Gently flip it over, slipping your hand out just before it hits the grill. If it is slightly wopperjawed (a technical term, ha), push it back in place and line it up. Leave it to cook undisturbed until golden brown. By the time the second side is done, the top will be cool enough to touch, helping you keep the sandwich together as you transfer it from the grill or pan to the cutting board.

Gluten-Free Tips:

If you are using gluten-free bread, lightly toast it before assembling the sandwiches and putting them on the grill. Gluten-free bread typically suffers from an odd texture, making it seem underbaked. Toasting it first will add crunch and help keep it from absorbing the extra liquid from the cheese and tomatoes.

Caprese Grilled Cheese Sandwiches; 2014 Jane Bonacci, The Heritage Cook

Caprese Grilled Cheese Sandwiches
Yields 4
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  1. 8 slices sandwich or gluten-free bread
  2. Butter, at room temperature
  3. 8 oz fresh mozzarella cheese (packed in water)
  4. 4 oz white cheddar cheese, shredded
  5. 2 or 3 fresh ripe tomatoes, cored and cut into 1/4-inch thick slices
  6. Fresh basil leaves, rinsed and patted dry with paper towels
  7. Kosher salt and freshly ground black pepper
  1. Preheat your gas grill to medium-high; or build a medium charcoal fire.
  2. Brush one side of each piece of bread with butter. (Lightly toast slices if you are using gluten-free bread.) Place the bread in four stacks of two slices, buttered sides together on a platter.
  3. Drain the mozzarella and, using a sharp knife, slice into thin pieces. You want at least eight slices so you can use two per sandwich. Place on the platter next to the bread and add the shredded Cheddar. Put a couple layers of paper towel on platter and place the tomato slices in it to absorb extra liquid.
  4. Stack the basil leaves about 5 to 8 leaves high and roll into a tight “cigar”. Use a sharp knife to slice crosswise very thinly. This creates little ribbons of basil called "chiffonade."
  5. When the grill is hot, start assembling your sandwiches. On the unbuttered side of four slices of the bread, layer some of the cheddar, 2 slices of tomato, a slice or two of mozzarella, salt and pepper to taste, and a sprinkling of the basil chiffonade.
  6. Use a spatula to transfer the bread slice with topping to the grill, leaving the second piece of bread on the platter. Place the remaining slice of bread, buttered side up, on top of the fillings and press gently.
  7. Cook on the first side until you have nice grill marks and the cheeses are starting to melt. Use a spatula to flip each sandwich, using your other hand to hold the sandwich together. Cook the second side until you have grill marks and the cheese has melted.
  8. Carefully transfer to a cutting board and slice in half diagonally. Serve immediately.
The Heritage Cook ®

Create a New Tradition Today!

This recipe is part of Food Network’s weekly Summer Soiree. See the links below for more inspiration and great recipes and check out our Pinterest page for all the recipes from the past year!

The Lemon Bowl: Tart Cherry Chinese BBQ Pulled Pork
Feed Me Phoebe: Grilled Lamb Kebabs with Lebanese Tomato Salsa
Weelicious: Southern-Style Pork Tenderloin
The Heritage Cook: Caprese Grilled Cheese Sandwiches (Gluten-Free)
Napa Farmhouse 1885: BBQ Pork Ribs
Red or Green: BBQ Salmon with Hot Pepper Jelly Glaze and Marinated Tomatoes
Domesticate Me: Fiery Barbecue Flank Steak Tacos with “Summer Mess” Salsa
Devour: 5 BBQ Sandwiches
In Jennie’s Kitchen: Ginger-Soy Marinated Flank Steak
FN Dish: The Beauties of Barbecue

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  1. Carol says

    This looks wonderful Jane! What a lovely way to enjoy all of fresh tomatoes and basil from this summer’s harvest.

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