Preheat your oven to 425 degrees F. Lay a rimmed baking sheet with foil for easy cleanup. This will help roast the vegetables and make it easier to clean up later.
Prepare the tomatoes by removing their stems and discarding them. For plum or Roma tomatoes, cut them in half, slice vine tomatoes into wedges, and leave cherry tomatoes whole for a touch of texture.
Arrange the prepared tomatoes on the baking sheet. Add the smashed garlic cloves and wedges of onion to the mix. Drizzle the mixture with olive oil, then sprinkle generously with kosher salt and freshly-ground black pepper to enhance the flavors. Toss everything together to coat.
Nestle the sprigs of thyme and the oregano beneath and around the tomatoes. This will infuse the soup with wonderful herbaceous notes as it roasts.
Roast in the oven for about one hour, or until the tomatoes, onions, and garlic are soft, caramelized, and bubbling with goodness. Make sure to keep an eye on them so they don’t burn.
Once roasted, remove the herb sprigs from the tray and discard them. Transfer the roasted tomatoes, onions, and garlic into a large, heavy-bottomed pot, capturing any delicious juices that have released.
Add in two cups of broth and bring the mixture to a boil over medium-high heat. Then, reduce the heat and let it simmer for about twenty-five minutes. This allows the flavors to meld beautifully.
Stir in the torn basil leaves along with the reserved thyme and let the soup simmer for an additional three to five minutes, just until the basil wilts.
Now it’s time to puree the soup! You can transfer it in batches to a blender or use an immersion blender directly in the pot. If using a blender, be careful not to fill it more than halfway, as hot liquids expand.
If you prefer, strain the soup through a mesh sieve to remove any seeds or bits of skin for a smoother texture.
Return the pureed soup to the pot. Stir in the heavy cream and taste. Season further with salt, pepper, and optional sugar to balance the flavors. Keep in mind that low-sodium broth may require more seasoning.
Serve the soup hot or chilled, garnished with croutons, fresh herbs, cracked pepper, or a swirl of cream. For an unbeatable pairing, enjoy it alongside a classic grilled cheese sandwich!
To store any leftovers, refrigerate them in an airtight container. It’ll stay fresh for three to four days, so you can enjoy this delightful soup again.
