First, roast the tomato and eggplant. Preheat the oven to 375 degrees. Place the whole tomatoes and garlic cloves on to a sheet pan, season them well with the salt and pepper. Oil them liberally with the extra virgin olive oil. Place 3 of the rosemary sprigs on top and then roast for about 25 minutes or until the tomatoes are well browned and softened.
Cut of the vine end of the eggplants. Standing the eggplants on the cut end, slice the eggplants in half north to south. Place them on a cutting board and score the flesh of the eggplant in an x pattern. Oil the flesh side well with the extra virgin oil and season them liberally with the salt and pepper. Add the remaining rosemary to the top of the eggplant. Place into the oven and roast until the flesh is soft enough to be scooped out with a spoon, about 30 minutes. Let cool.
Place a large soup pot onto a stove top and heat on medium heat. Add about 4T of olive oil and then add the onions and fennel. Sweat until they are soft, about 8 minutes. Add the roasted tomatoes and garlic as well as all of the liquid from the pan. Remove the skin from the eggplant, and then add all of the eggplant flesh and rosemary into the pot. Add the water and then bring to a simmer. Simmer for about 40 minutes.
In batches, blend the soup until smooth. Again, check the soup for seasoning before serving.