Prepare the herb-roasted tomatoes by roasting fresh tomatoes with olive oil, garlic, and herbs until caramelized.
For the candied bacon, bake bacon strips coated in a mixture of brown sugar and spices until crispy and sweet. Chop into medium-sized pieces and set some aside for garnish.
Preheat the oven to 400°F (200°C) and line a baking sheet with parchment paper.
Spread garlic herb butter on the outside of each bread slice. On the inside of two slices, add a generous amount of shredded cheddar cheese. Top with the remaining slices, buttered side out, to form sandwiches.
Place the sandwiches on the prepared baking sheet, cover with parchment paper and another baking sheet to press them down. Bake for 10-15 minutes or until golden and crispy. Let cool before cutting into crouton-sized squares.
Heat olive oil in a medium Dutch oven over medium-high heat. Sauté the chopped onions and garlic until translucent and fragrant, about 1-2 minutes. Stir in garlic powder, smoked paprika, oregano, thyme, red pepper flakes, and tomato paste. Cook for another minute until well combined.
Transfer the sautéed ingredients to a blender along with the roasted tomatoes, candied bacon, and vegetable or chicken stock. Blend on high until smooth.
Return the blended mixture to the Dutch oven. Stir in heavy cream, cooking wine (if using), Parmesan cheese, and maple syrup. Bring the soup to a gentle boil for 1-2 minutes, then reduce to a simmer for 5-6 minutes.
Add the cornstarch mixture, stirring until fully dissolved and the soup thickens to your desired consistency. Season with salt and black pepper to taste.
Ladle the bisque into bowls and top with grilled cheese croutons, chopped candied bacon, freshly grated Parmesan, and parsley. Serve warm and enjoy!
