For the soup:
8 large (about 4 pounds) tomatoes, stemmed and quartered
½ cup extra virgin olive oil, divided
1 head garlic (about 12 cloves), peeled and lightly crushed
Freshly ground sea salt, to taste
Freshly ground black pepper, to taste
Crushed red pepper, to taste
1 cup chopped sweet onion
½ cup vegetable stock
1 cup half and half (regular or fat free)
1 tsp sugar
½ cup basil, chopped (3/4 oz container from the produce department)
For the Crostini:
1 crusty baguette
Extra virgin olive oil
Freshly ground sea salt
Preheat the oven to 500 degrees F. In a 13x9 non-reactive baking dish, place the stemmed and quartered tomatoes, ¼ cup of the olive oil, garlic cloves, and some sea salt; toss to coat. Roast the tomatoes in the oven until very dark in spots, 35-40 minutes. Remove and allow them to cool for a bit.
For the crostini, cut the bread into 1/8 inch slices on a bias. Lightly brush both sides with olive oil and sprinkle with sea salt, place on a baking sheet, and toast in the oven until golden brown and slightly crisp, about 6 minutes.
In a large saucepan over medium heat, combine the remaining ¼ cup of olive oil, the chopped onions, a pinch of salt, a pinch of black pepper, and a pinch of crushed red pepper.
Sauté until the onion is translucent, stirring occasionally, about 8 minutes. Add the basil leaves and stir to combine, sauté for about 1 minute. Add the roasted tomatoes and the vegetable stock to the onion mixture, add a pinch of sugar, bring to a simmer, and allow it to cook for 10 minutes. Add the mixture to a blender or food processor, along with the 1 cup of half and half, and pulse until desired consistency.
Re-season with salt and pepper if necessary, return to the pan, and heat through. Serve the soup with the crostini for dipping.