Preheat your grill to 350 degrees. Create a direct and indirect heating zone (the tomatoes will be grilled direct, crostini indirect). Slice your tomatoes in half and drizzle them in a little olive oil.
Grill the tomatoes until the form a nice char on both sides, this will take approximately 15 minutes (give or take), depending on your grill. Once your tomatoes are nice and charred, put them in a deep sauce pot and put them on the stove. Using an immersion blender, blend the tomatoes together. Next, add the chicken broth and remaining ingredients. Blend until smooth. Place the pot on low-medium heat so the soup will be warm for serving.
Now, take a baquette and make 1/2 inch or smaller slices. Coat them in olive oil on both sides. Grill the crostini on indirect heat until toasted, about 2 minutes each side. Remove from grill and layer crostini, cheese, meat, peppers, and arugula and repeat, sandwiching a crostini on each each. Stick a skewer in through the middle to keep the pieces together. Serve with the soup for a sassy presentation that is perfect for dipping in the soup!
Alas, this is one of those recipes that I just made that turned out wonderfully. I love those redeeming recipes that come out so great, to make up for the ones that don't. I hope you enjoy!