AW Eats
About the Recipe
This is one of those meals I remember dearly from my childhood—a timeless, old-school combo that never loses its magic. On cold winter days, there was nothing better than a warm bowl of tomato soup paired with a perfectly melty grilled cheese. This version honors that memory with real care: slow-cooked aromatics, roasted garlic, and good tomatoes for the soup, and a thoughtful trio of cheeses on hearty bread for the sandwich. It’s the kind of comfort that wraps you up and brings you right back home.
Ingredients
For the Tomato Basil Soup
2 tbsp olive oil
1 large yellow onion, finely diced
2 carrots, peeled and diced
2 celery stalks, diced
Kosher salt, to taste
1 bulb roasted garlic (about 6–8 cloves)
3 tbsp tomato paste
1/2 cup dry white wine
2 (28 oz) cans whole San Marzano tomatoes, passed through a food mill
3 cups homemade chicken stock (or vegetable stock)
1–2 tsp granulated sugar, or to taste
1 large Parmesan rind (optional but recommended)
1 tsp dried oregano
1 tsp crushed red pepper flakes (optional)
1 large bunch fresh basil (about 1 cup, packed)
1/2 cup heavy cream
Freshly ground black pepper, to taste
Fresh basil (thinly sliced, for garnish)
Freshly grated Parmesan, for garnish
For the Triple Cheese Grilled Cheese
8 slices sourdough bread (or similar hearty artisan bread)
4 tbsp mayonnaise (for bread exterior)
4 oz sharp white cheddar, shredded
4 oz fontina, shredded
4 oz mozzarella, shredded
2 tbsp butter, for griddling
Preparation
Tomato Basil Soup
In a large pot, heat olive oil over medium heat. Add onion, carrot, and celery. Season with salt and cook until softened and fragrant, about 10–12 minutes.
Stir in roasted garlic and tomato paste. Cook for 3–4 minutes until the paste darkens slightly and caramelizes.
Deglaze the pot with white wine, scraping up any bits from the bottom. Let the wine reduce by half, about 3–5 minutes.
Add the milled tomatoes and stock. Add sugar along with the Parmesan rind, oregano, red pepper flakes, and fresh basil leaves.
Season generously with salt and pepper. Simmer uncovered over low heat for 45–60 minutes, stirring occasionally, until the soup has reduced and developed a deep flavor.
Remove the Parmesan rind and blend the soup in batches until smooth, or use an immersion blender directly in the pot.
Strain the blended soup through a fine mesh strainer into a clean pot or bowl, pressing with a spoon to extract all the liquid. Discard solids.
Stir in heavy cream and adjust seasoning to taste.
Ladle into bowls and garnish with sliced basil and freshly grated Parmesan.
Triple Cheese Grilled Cheese
Heat a skillet or griddle over medium-low heat.
In a bowl, mix the three shredded cheeses together.
Spread a thin layer of mayonnaise on the outside of each bread slice.
Assemble sandwiches with a generous amount of cheese mixture between two slices of bread (mayonnaise side out).
Melt a bit of butter on the skillet and place the sandwiches down. Cook slowly for 3–4 minutes per side, pressing gently, until golden brown and crispy, and the cheese is fully melted.
Slice diagonally and serve warm with the tomato basil soup.