Cozy Up This Winter: The Ultimate Cornbread Waffle Grilled Cheese Sandwich with Creamy Tomato Basil Soup
As the crisp chill of winter settles over Denver, there’s an undeniable craving for warmth and comfort that begins to take hold. The leaves have long since fallen, and the air bites with a cold that makes you feel it deep in your bones the moment you step outside. It’s truly the season for embracing all things cozy, and for me, that means indulging in the kind of food that wraps you in a warm hug from the inside out.
There’s something inherently nostalgic and incredibly satisfying about comfort food. It’s more than just a meal; it’s a feeling, a memory, a moment of pure bliss. And few dishes evoke that feeling quite like a classic grilled cheese sandwich paired with a steaming bowl of rich tomato soup. It’s a timeless combination that resonates with many, bringing a sense of warmth and contentment to both the heart and the stomach. This recipe, however, takes that beloved duo and elevates it to an extraordinary level, transforming a simple meal into an unforgettable culinary experience.

The Elevated Grilled Cheese: Cornbread Waffles Meet Melted Perfection
Imagine a grilled cheese sandwich, but instead of traditional bread, it’s crafted between two warm, buttery cornbread waffles. This isn’t just a twist on a classic; it’s a revelation. The cornbread waffles bring a delightful sweetness and a unique texture that ordinary bread simply cannot. Their distinctive nooks and crannies become perfect pockets for capturing the molten cheese, ensuring every bite is bursting with flavor and gooey goodness. The slight crispness of the waffle exterior, achieved through a gentle grilling, contrasts beautifully with the soft, yielding interior and the luscious, melted cheese within.
Choosing the right cheese is crucial for a truly magnificent grilled cheese. For this recipe, a blend of sharp cheddar and creamy Monterey Jack creates a harmonious balance. The cheddar offers a robust, tangy flavor, while the Monterey Jack provides that incredible stretch and velvety texture when melted. This combination ensures a rich, satisfying filling that oozes tantalizingly from the waffle. Each waffle half is lightly buttered and then filled with a generous amount of this cheesy mixture, transforming into golden, crispy parcels of pure joy when grilled.

Beyond the Can: A Journey to Authentic Tomato Flavor
My appreciation for a truly exceptional tomato soup didn’t happen overnight. For years, like many, I relied on canned versions during my college days – quick, cheap, and convenient. However, a transformative experience living in Italy forever changed my perspective. The tomatoes there were unlike anything I had ever tasted: deeply flavorful, intensely sweet, and vibrant. It was a culinary awakening, teaching me the profound impact that high-quality, authentic ingredients can have on a dish. This revelation made it impossible to return to the lackluster taste of processed, tin-can soups.
Since then, I’ve made it a mission to seek out the best possible tomatoes for my kitchen, striving to recreate that rich, sun-kissed flavor I discovered abroad. This commitment led me to products like Pomì tomatoes, which stand out for their exceptional quality. Sourced from the finest Italian fields, these tomatoes boast an incredible depth of flavor that genuinely shines through in any recipe. They are the secret weapon behind this creamy tomato and basil soup, elevating it from a simple side dish to a star in its own right.

The Heart of the Meal: Creamy Tomato Basil Soup
What makes this creamy tomato basil soup truly special is its reliance on the natural goodness of premium ingredients, specifically Pomì chopped and strained tomatoes. Because their flavor is so incredibly robust and fresh, the soup recipe remains delightfully simple. You won’t find a laundry list of spices trying to mask an inferior taste; instead, a few key aromatics and seasonings are all that’s needed to enhance the inherent sweetness and acidity of the tomatoes. Sautéed onions, dried basil, oregano, and a hint of garlic powder create a fragrant base that complements the tomatoes perfectly, building layers of savory goodness.
After a gentle simmer, which allows all the flavors to meld beautifully, the soup is then blended to a velvety smoothness. A touch of heavy cream is stirred in at the end, lending a luxurious, silken texture and tempering the acidity of the tomatoes, resulting in a perfectly balanced and incredibly comforting soup. It’s a rich, smooth, and deeply satisfying experience that feels both gourmet and familiar. This soup isn’t just an accompaniment; it’s an integral part of the experience, offering a vibrant, warm counterpoint to the savory grilled cheese.

The Perfect Pair: Dipping into Delight
The magic of this meal truly comes alive when these two components are brought together. Imagine dipping a crisp, cheesy cornbread waffle quarter into the warm, creamy tomato basil soup. The crunch of the waffle, the stretch of the melted cheese, and the burst of rich, acidic tomato flavor create a symphony of textures and tastes in every mouthful. The hearty nature of the cornbread waffle means it holds up beautifully to dipping, absorbing just enough of the soup to become wonderfully tender without becoming soggy. It’s a sensory experience that defines comfort food.
This dish is not just for cold winter nights; it’s perfect for any occasion when you crave something wholesome, satisfying, and utterly delicious. It’s a fantastic option for a family dinner, a cozy lunch, or even a comforting meal prep solution. The soup can be made in advance and gently reheated, making weeknight meals a breeze. Garnish the soup with a sprinkle of fresh chopped basil for an extra layer of aroma and visual appeal, or even a few homemade croutons for added crunch. This elevated take on a classic offers a gourmet touch to a beloved comfort food, promising smiles all around.

Tips for Crafting Your Own Comfort Masterpiece
Making this Cornbread Waffle Grilled Cheese Sandwich with Tomato Basil Soup is straightforward, but a few tips can ensure your meal is absolutely perfect. For the cornbread waffles, make sure your waffle iron is adequately preheated and well-greased to prevent sticking and ensure a beautiful golden crust. Don’t overmix the batter; a few lumps are fine and will result in a tender waffle. When assembling the grilled cheese, feel free to experiment with your favorite cheese blends. Provolone, Gruyere, or even a spicy pepper jack could add an exciting twist.
For the soup, while Pomi tomatoes are highly recommended for their superior quality, ensure whatever brand you choose is of excellent standard, as the tomatoes are the undeniable star. Adjust the seasonings to your preference; a little extra red pepper flake can add a pleasant warmth, or a swirl of pesto can introduce an herbaceous layer. If you’re looking to make this a complete meal, a simple green salad with a light vinaigrette would be a wonderful accompaniment, cutting through the richness of the main dish. This recipe is an invitation to explore and customize, allowing you to create your ultimate comfort food experience.
So this week, treat yourself and your loved ones to this incredible combination. It’s more than just dinner; it’s an experience of warmth, flavor, and pure comfort that will leave everyone feeling nourished and happy. Gather your ingredients and prepare to transform a classic into a culinary delight!
If you’re looking for more incredible ways to use these ridiculously fresh and flavorful chopped and strained tomatoes from Pomì, be sure to check out Pomì’s online cookbook! It’s FREE and offers a wealth of inspiring recipes perfect for any season.
Disclosure: I received free product and compensation from Pomì as part of this post. As always, all opinions and recipe are my own. Thanks for supporting the brands that support Cake ‘n Knife!

Cornbread Waffle Grilled Cheese Sandwich with Tomato Basil Soup
ingredients
For the Cornbread Waffles
- 1 3/4 cups all-purpose flour
- 1 1/4 cups cornmeal
- 1 Tbsp baking powder
- 1 tsp granulated sugar
- 1 tsp salt
- 2 cups milk
- 3 Tbsp vegetable oil
- 2 large eggs
For the Grilled Cheese Filling
- 1 cup shredded cheddar cheese
- 1 cup shredded Monterey Jack cheese
For the Creamy Tomato Basil Soup
- 2 tsp olive oil
- 1/2 large onion diced
- 2 Tbsp dried basil
- 1/2 Tbsp dried oregano
- 1/2 tsp garlic powder
- 1/4 tsp salt
- 1/4 tsp black pepper
- Pinch of red pepper flakes (optional, for a touch of heat)
- 1 container (26.46 oz) Pomì Chopped Tomatoes
- 1 cup Pomì Strained Tomatoes
- 1 cup chicken broth
- 1/3 cup heavy cream
instructions
For the Creamy Tomato Basil Soup:
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In a large saucepan or Dutch oven, heat 2 teaspoons of olive oil over medium-high heat. Once the oil is shimmering, add the diced onion and cook until it is softened and lightly browned, which should take approximately 3 to 5 minutes.
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Stir in the dried basil, dried oregano, garlic powder, salt, black pepper, and a pinch of red pepper flakes (if using). Cook for about 1 minute until fragrant.
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Add the Pomì chopped tomatoes, Pomì strained tomatoes, and chicken broth to the saucepan. Bring the mixture to a boil, then reduce the heat to medium-low and let it simmer gently for 20 minutes, allowing the flavors to meld and deepen.
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Remove the saucepan from the heat. Carefully transfer the hot soup mixture to a blender (working in batches if necessary, filling the blender no more than halfway). Puree until the soup is completely smooth and creamy. Return the pureed soup to the saucepan.
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Stir in the heavy cream and combine on low heat until warmed through. Keep the soup warm while you prepare the grilled cheese sandwiches.
For the Cornbread Waffle Grilled Cheese:
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In a medium mixing bowl, whisk together the dry ingredients for the cornbread waffles: flour, cornmeal, baking powder, sugar, and salt.
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In a separate bowl, whisk together the wet ingredients: milk, vegetable oil, and eggs. Pour the wet ingredients into the dry ingredients and stir until just combined and smooth. Be careful not to overmix.
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Preheat your waffle iron and lightly grease it with cooking spray or butter. Pour 1/2 cup to 3/4 cup of the cornbread batter onto the hot waffle iron (depending on its size), close, and cook until golden brown and thoroughly cooked through. This usually takes 3-5 minutes. Repeat with the remaining batter to make several waffles.
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Once you have prepared enough cornbread waffles (you’ll need two per sandwich), it’s time to assemble the grilled cheese. Place one cornbread waffle on a clean surface. Sprinkle 1/2 cup of the shredded cheddar cheese evenly over the waffle, then top with 1/2 cup of the shredded Monterey Jack cheese. Place a second cornbread waffle on top to form a sandwich. Repeat for additional sandwiches.
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Heat an oiled skillet over medium-high heat. Carefully place the cornbread waffle sandwich in the hot skillet. Cook for approximately 2 to 3 minutes per side, or until the cornbread is golden brown and crispy, and the cheese is thoroughly melted and gooey.
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Once cooked, remove the sandwich from the skillet and cut it into quarters. Repeat the grilling process for any remaining sandwiches.
To Serve:
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Serve one generous bowl of warm tomato basil soup with two quarters of the cornbread waffle grilled cheese. Garnish with fresh chopped basil, if desired, for an extra touch of freshness and aroma. Enjoy immediately!
Pin this Cornbread Waffle Grilled Cheese Sandwich with Tomato Basil Soup recipe for later to savor this ultimate comfort meal!
