Ultimate Comfort: Cornbread Waffle Grilled Cheese Sandwich with Homemade Tomato Basil Soup
When the temperature drops and the world outside turns crisp, there’s nothing quite like a meal that wraps you in a warm hug from the inside out. This isn’t just any comfort food; it’s a culinary embrace that perfectly marries two beloved classics with an innovative twist. Imagine warm, golden, and slightly sweet cornbread waffles, crisp on the outside and tender within, generously stuffed with an irresistible blend of gooey, melted cheese. This delectable creation is then served alongside a bowl of the creamiest, most aromatic homemade tomato basil soup, brimming with deep, rich flavors. It’s a combination designed to bring a smile to anyone’s face and pure contentment to their tummy, proving that some pairings are simply meant to be.

Embracing the Chill: Our Winter Comfort Food Craving
Here in Denver, the shift from vibrant autumn to the stark beauty of winter has been swift and undeniable. The air carries a distinct chill, visible as a wisp of breath in front of me, and the cold penetrates to the chest the moment I step outdoors. Fall’s fleeting colors have given way to the crisp, clear days and long, dark nights that signal winter’s firm arrival. And with it, an undeniable craving settles in – a deep-seated desire for hearty, soul-warming meals that offer solace and satisfaction. It’s officially the season to indulge in all the glorious comfort food imaginable, dishes that don’t just fill your stomach but also nourish your spirit.

There are few combinations as universally beloved and inherently comforting as a perfectly grilled cheese sandwich served alongside a steaming bowl of tomato soup. Just thinking about it conjures a profound sense of warmth and nostalgia. It’s a meal that transcends generations, reminding us of simpler times and the pure joy of good food. But today, we’re not just making any grilled cheese and tomato soup; we’re elevating it to an art form, giving it a gourmet yet approachable twist that will redefine your definition of comfort food.
From College Cans to Culinary Excellence: The Journey to Better Soup
For many years, my go-to for tomato soup was the ubiquitous canned variety, a trusty companion through countless cheap college meals. While it served its purpose during those leaner days, my palate has thankfully evolved. My time spent immersed in the culinary wonders of Italy ignited a profound appreciation for the humble tomato. The tomatoes there were unlike anything I had ever tasted – deeply flavorful, incredibly vibrant, and bursting with a natural sweetness and acidity that could only come from sun-drenched fields and rich soil. It was a revelation that transformed my understanding of what a tomato should taste like.

This newfound appreciation for quality ingredients is precisely why I now meticulously seek out exceptional products, such as Pomì tomatoes, for my kitchen. Pomì sources only the highest quality Italian tomatoes, and the difference in taste is genuinely remarkable. Using their chopped and strained tomatoes ensures that my creamy tomato and basil soup achieves an unparalleled depth of flavor and luxurious richness. It transforms a simple soup into a gourmet experience, making it the perfect indulgent companion to our unique cornbread waffle grilled cheese. The quality of the tomatoes truly shines through, allowing the natural sweetness and tang to be the stars of the dish.
The Star of the Show: Cornbread Waffle Grilled Cheese
Why cornbread waffles for grilled cheese, you ask? Because innovation in comfort food is always a good idea! Traditional bread is wonderful, but cornbread waffles offer an entirely new dimension of flavor and texture. The subtle sweetness and distinct, slightly gritty texture of cornbread provide a delightful contrast to the salty, gooey cheese. When cooked in a waffle iron, the cornbread develops a beautifully crisp exterior and those signature nooks and crannies that are absolutely perfect for trapping all that delicious melted cheese. Each bite offers a satisfying crunch, followed by the soft, warm interior and the irresistible pull of two types of perfectly melted cheese – sharp cheddar and creamy Monterey Jack. This unique base elevates the classic grilled cheese from a simple sandwich to a truly memorable meal, offering a textural journey that traditional bread simply cannot match.

The beauty of this combination is in its simplicity, yet profound flavor. The melted cheese oozes into every single nook and cranny of the cornbread waffle, creating pockets of rich, savory deliciousness. And then there’s the soup – a testament to how exceptional ingredients can speak for themselves. The rich, slightly acidic Pomì tomatoes burst with authentic flavor in every spoonful. Our tomato basil soup recipe is intentionally simple precisely because you don’t need a heavy hand with spices to mask any “tin can” taste; there isn’t any! What you get is nothing but pure, rich, smooth, and utterly delicious tomato perfection, enhanced by aromatic basil and a hint of warming spices.
Elevating Your Comfort Food Game: Tips for the Perfect Pair
Creating this ultimate comfort meal is straightforward, but a few tips can ensure perfection:
- For the Waffles: Don’t overcrowd your waffle iron. Give each cornbread waffle enough space to cook evenly and achieve that desired golden-brown crispness. A light brushing of oil or cooking spray on the iron before each batch is essential.
- The Cheese Blend: The combination of sharp cheddar and Monterey Jack offers both robust flavor and incredible meltability. Feel free to experiment with other cheeses like Gruyère for a nutty touch or pepper jack for a hint of spice. The key is using cheese that melts well.
- Perfect Grilled Cheese: Cook your cornbread waffle grilled cheese over medium-high heat in an oiled skillet. This ensures a beautifully golden exterior and fully melted, gooey interior without burning the waffles. Don’t rush it!
- Soup Smoothness: After simmering, blending the soup until completely smooth is crucial for that luxurious, creamy texture. An immersion blender works wonders for this directly in the pot, saving you from transferring hot liquid to a traditional blender.
- Serving Suggestion: While this meal is perfect on its own, a sprinkle of fresh chopped basil or a dollop of crème fraîche on the soup can add a beautiful finish. Consider a light side salad for a touch of freshness to balance the richness.

A Modern Classic for Your Dinner Table
This week, step up your dinner game and transform a beloved childhood classic into a sophisticated yet utterly comforting meal. Whether you’re feeding your family, hosting friends, or simply treating yourself, this Cornbread Waffle Grilled Cheese Sandwich with Tomato Basil Soup is guaranteed to be a hit. It’s a grown-up twist on a timeless favorite, showcasing how simple, high-quality ingredients and a little creativity can elevate everyday dishes into extraordinary culinary experiences. Prepare to be amazed by the depth of flavor and the comforting embrace of every single bite.
If you’re eager to discover more incredible ways to utilize the ridiculously fresh and flavorful chopped and strained tomatoes from Pomì, make sure to explore Pomì’s online cookbook! It’s completely FREE and packed with delicious recipes that won’t contribute to extra holiday weight – leaving more room for those essential holiday cookies, of course!
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
- 1 3/4 cups flour
- 1 1/4 cups cornmeal
- 1 Tbsp baking powder
- 1 tsp sugar
- 1 tsp salt
- 2 cups milk
- 3 Tbsp vegetable oil
- 2 eggs
- 1 cup shredded cheddar cheese
- 1 cup shredded monterey jack cheese
- 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 pepper
- Pinch of red pepper flakes
- 1 26.46 oz Pomi Chopped Tomatoes container
- 1 cup Pomi Strained Tomatoes
- 1 cup chicken broth
- 1/3 cup heavy cream
instructions
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In a large saucepan, heat 2 tsp olive oil over medium-high heat. When hot, add onion and cook until browned, approximately 3 to 5 minutes. Add basil, oregano, garlic powder, salt, pepper, red pepper flakes, Pomi chopped tomatoes, Pomi strained tomatoes and chicken broth. Bring to a boil, then reduce to a simmer over medium-low heat. Simmer for 20 minutes.
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Remove from heat and add to a blender. Puree until smooth. Add heavy cream and combine on low. Keep warm.
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In a medium bowl, whisk together flour, cornmeal, baking powder, sugar and salt for the cornbread waffles. Add milk, vegetable oil and eggs, stirring until smooth.
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Grease a waffle iron with cooking spray. Add 1/2 cup to 3/4 cup to your waffle iron, cooking until golden brown and cooked through. Once you’ve created at least 4 waffles, make the grilled cheese!
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Add 1/2 cup of each type of cheese between two cornbread waffles to create a sandwich. Cook in an oiled skillet over medium-high heat until golden brown and the cheese is melted, approximately 2 to 3 minutes per side. Cut into quarters. Repeat with the second set of waffles.
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Serve one bowl of soup with two quarters of each cornbread grilled cheese. Garnish with fresh chopped basil as desired.
Don’t forget to save this delicious Cornbread Waffle Grilled Cheese Sandwich with Tomato Basil Soup recipe to your Pinterest board for easy access later!
