Roasted Tomato Garlic Soup with Grilled Cheese

Instructions

1. Prepare the oven and vegetables. Preheat the oven to 425°F (220°C). Arrange the tomato halves and onion quarters on a large baking tray in a single layer. Leave some space between them so they roast evenly.
2. Prepare the garlic. If using a whole bulb, slice about ¼ inch off the top to expose the cloves. Set it on the tray, cut side up, and drizzle it with a little olive oil. If using peeled cloves, tuck them close to the tomatoes or beneath an onion piece so they do not burn.
3. Season and roast. Drizzle the remaining olive oil over the tomatoes and onion. Sprinkle with oregano, basil, salt, and pepper. Roast for 30–35 minutes, until the vegetables are soft and the tomato edges are slightly caramelized. Check the garlic near the end; it should be tender, not dark brown.
4. Blend the soup. Let the vegetables cool for a few minutes. If you roasted a whole garlic bulb, squeeze the softened cloves out of their skins. Add the roasted vegetables, garlic, and any juices from the tray to a blender with the broth. Blend until smooth. Work in batches if needed, and leave the blender lid vented according to its instructions when blending hot ingredients. For a more textured soup, use an immersion blender in the pot instead.
5. Finish on the stove. Pour the blended soup into a pot. Stir in the heavy cream and tomato paste, if using. Simmer gently over low heat for 5–10 minutes, stirring occasionally. Taste before adding more salt or pepper, since the broth may already be seasoned. If the soup is thicker than you like, stir in a splash of broth or water.
6. Make the grilled cheese. While the soup simmers, place cheese between pairs of bread slices. Spread butter on the outside of each sandwich. Heat a skillet over medium heat and cook the sandwiches for 2–3 minutes per side, pressing lightly with a spatula. They are ready when the bread is golden and the cheese has melted. Lower the heat if the bread browns before the cheese melts.
7. Serve. Ladle the hot soup into four bowls. Add a small swirl of cream and a sprinkle of basil or pepper if you like. Serve each bowl with a grilled cheese sandwich.

Tips

Choose flavorful tomatoes. Ripe tomatoes give the soup the best balance of sweetness and acidity. If your tomatoes are very small, use a few extra. The roasting step deepens their flavor, so allow them to soften fully and develop a little color around the edges.

Use the roasting juices. The liquid left on the baking tray contains plenty of tomato and garlic flavor. Carefully scrape it into the blender with the vegetables. If browned bits are stuck to the tray, a small splash of broth can help loosen them.

Adjust the texture. Blend longer for a creamy, even consistency. If you prefer a very smooth soup, pass it through a fine-mesh strainer after blending. For a thicker soup, start with slightly less broth and add more only if needed. Keep the heat low after adding the cream to prevent a hard boil.

Pick the cheese you enjoy. Cheddar gives the sandwich a sharper flavor, while mozzarella makes it mild and stretchy. You can combine the two. Use enough cheese to cover the bread in an even layer, but avoid overfilling the sandwich so it cooks neatly.

Keep the timing simple. Start the grilled cheese during the soup’s final simmer. This lets you serve both while they are hot. If your skillet only fits one sandwich at a time, keep the finished sandwiches on a tray in a low oven until the rest are ready.

Storage

Allow leftover soup to cool, then transfer it to an airtight container. Refrigerate for up to 3 days. Reheat in a pot over low to medium-low heat, stirring occasionally. Add a splash of broth or water if it thickens in the refrigerator. Heat it until steaming, but avoid boiling it vigorously after the cream has been added.

You can also freeze the soup for up to 2 months. For the best texture, freeze it before adding the cream, then stir in the cream after thawing and reheating. If the finished creamy soup has already been frozen, stir or blend it briefly after reheating if it separates.