Preheat the oven to 450 degrees F. Core and halve the tomatoes (leave the cherry tomatoes whole). Heat a flameproof roasting pan over medium-high heat. Drizzle with the 1/2 cup olive oil, then spread all of the tomatoes, the garlic and onions in the pan. Cook, stirring gently, until the garlic is browned, about 5 minutes. Season with salt and pepper. Transfer the pan to the oven and roast until the tomatoes are caramelized, 20 to 30 minutes.
Remove the roasted tomatoes, garlic and onions from the oven and transfer to a large stockpot (set aside the cherry tomatoes for garnish). Add 3 cups chicken stock, the bay leaves and butter. Bring to a boil, then reduce the heat to medium and simmer until the liquid is reduced by one-third, 15 to 20 minutes. Remove the bay leaves.
Add the basil to the pot. Use an immersion blender to puree the soup until smooth (or puree in a regular blender and return to the pot). Reduce the heat to low, add the heavy cream and adjust the consistency with the remaining 1 cup chicken stock, if necessary. Season with salt and pepper. Divide among bowls and top with the roasted cherry tomatoes; drizzle with olive oil.
Serve with Grilled Cheese with Apple and Bacon.
Grilled Cheese with Apple and Bacon
Spread dijon mustard on 4 slices country white bread. Top with sliced cheddar cheese, cooked bacon and sliced Granny Smith apple, then top with 4 more slices bread. Butter the sandwiches, then cook in a skillet over medium-low heat until the cheese melts and the bread is golden, about 3 minutes per side.