Preheat oven to 450F.

Add the quartered tomatoes, chopped yellow onion, halved honey nut squash, and garlic. If using the whole garlic head, slice the very top off to reveal the cloves inside. Drizzle generously with olive oil, then season with salt and black pepper.

Roast for 15-20 minutes, until tomatoes are juicy and vegetables tender.

Let cool to room temperature, then transfer all vegetables and juices to a high speed blender. If using the whole garlic head, squeeze the cloves out of their skins. Use a spoon to scoop out the honey cut squash from its exterior. Add the basil. Blend until very smooth.

In a large soup pot over medium high heat, combine the butter and flour. Mix until a roux forms, about 1 minute. Stir in the honey.

Add the chicken broth, and as you stir, bring to a boil. Reduce heat to medium, then add the blended tomatoes. Stir until well-combined.

Bring to a boil once more, then simmer for 5-10 minutes. If desired, stir in the heavy cream.

Butter the outside pieces of your bread slices, then one slice butter-side down on a skillet over medium low heat. Add a generous serving of freshly grated medium cheddar and slice of havarti to the slice. Sandwich with the remaining buttered slice. Cook for 3-4 minutes, then flip to cook an additional 2-3 minutes, until golden brown on both sides and cheese is melted. Enjoy warm!