Preheat oven to 375 F.
Brush a foil-line baking sheet with olive oil and set aside.
Cut tomatoes in half and place cut side down on the prepared baking sheet.
Place onions and whole garlic cloves on the baking sheet.
Arrange everything in a single layer.
Roast for 35-45 minutes.
Remove from oven and let cool.
Remove the skins from the tomatoes (they should slip right off. You can leave the skin on the cherry tomatoes if you plan on blending it really well)
Peel cooled garlic and place into the blender, followed by the tomatoes, onions, basil and oregano.
Blend until smooth (or lightly chunky if you prefer.)
Transfer mixture to a large deep skillet or pot.
Stir in enough chicken broth just until your desired consistency is reached.
Bring to a simmer and simmer gently until hot.
You now have a GREAT base. Time to bring it to life!
Add in smoked salt and black pepper a little at a time until well seasoned being sure to taste after each addition. Salt & pepper really brings out the flavor!
Use white sugar to bring down the acidity and to lightly sweeten if needed.
Feel free to add in garlic powder, onion powder or dried oregano and parsley for more flavor.
Ladle soup into bowls & garnish with fresh basil and a splash of heavy cream.
To prepare the grilled cheese, heat griddle on medium heat.
Mix together mayonnaise, garlic and enough parsley for a pop of color.
Brush 4 slices of bread with the mayo mixture and place mayo side down on the griddle.
Spinkle on cheese.
Brush the top slices of bread with the mayo mixture and place on top of the cheese (mayo side up)
When the underside of the sandwiches are golden, flip over and allow the other side to turn golden.
(Press the sandwiches a little with a spatula to flatten.)
When both sides are golden, remove from griddle and cut into 3 sticks.
Serve alongside the tomato soup.