Preheat the oven to 400°F.
Line two baking sheets with foil.
Cut the 6 lbs. of Roma tomatoes in halves, lengthwise. If you are cutting a variety of tomatoes, like vine ripe or large red Beefsteak tomatoes, cut them in quarters. You want to cut the tomatoes the same size despite the varieties of tomatoes you use.
Place the cut tomatoes on the lined baking sheets.
Next, peel the outer layer of skins off the garlic cloves with your hands.
Next, with a sharp knife, cut the top half off each garlic clove.
Lay out three square sheets of foil.
Place each cut garlic clove on each foil square. You should have three foil squares with the garlic bottom and top on each one.
Next, drizzle at least 1 tbs. of extra virgin olive oil over each garlic clove. Next, sprinkle salt and pepper on each one. Wrap up and close the foil packets. Place on the baking sheet with the tomatoes.
Taking one cup of extra virgin olive oil, drizzle the oil across the tomatoes on the two sheet pans. Next, sprinkle salt and freshly ground pepper on the two baking sheets of tomatoes. I recommend using freshly ground black pepper using a pepper grinder for better flavor.
Bake the two sheet pans of tomatoes for 40 minutes.
About 10 minutes before the tomatoes are done roasting, begin prepping the fresh herbs. Separate the basil leaves from the stems, and set them aside. Separate the thyme leaves from the stems, and chop. Set aside.
Heat a large pot or Dutch oven over medium-high heat with 1 tbs. of olive oil. Once heated, throw in the chopped onions, and caramelize for 5 minutes.
By now, the tomatoes are done. Take them out of the oven, and let them cool for about 10 minutes while you finish cooking the onions. Open the garlic foil packets to speed up the garlic’s cooling process.
Once the onions are done caramelizing, reduce the heat to low, or turn off the stovetop altogether. Throw all of the tomatoes into the pot. Make sure to dump all of the tomato/oil juices from the pans into the pot.
Squeeze the garlic cloves out of the bulbs and into the pot.
Dump in the basil, fresh thyme, dried oregano, and red pepper flakes into the pot.
Blend the soup with a hand blender until fully blended. There should be no big chunks. If you don’t have a hand blender, you can use a regular blender, and pour the soup back into the pot.
Simmer the soup for 5-10 minutes, or until your desired temperature.
Taste test it, and add more salt and pepper if needed. In my experience, it doesn’t need it.
Serve the best tomato soup recipe with croutons, garlic bread, and grilled cheese, or serve by itself garnished with some extra basil.