2 1/2 pounds ripe heirloom tomatoes
1 small jalapeño, seeded and cut in half
6 cilantro sprigs
2 cloves garlic, coarsely chopped
2 tablespoons red wine vinegar
1/3 cup extra-virgin olive oil
1/4 cup diced red, yellow and orange sweet peppers
3 tablespoons diced shallots
small cherry tomatoes, cut in half
Blanch the tomatoes in boiling water for 30 seconds. Cool the tomatoes in a bowl of ice water a few minutes, and then use your fingers to slip off their skins. Remove the cores, and chop the tomatoes coarsely, saving all the juice. Reserve the ice water.
Seed and dice 1/4 cup worth of unpeeled cucumber, as nicely as you can for the garnish. Set aside. Peel and coarsely chop the remaining cucumbers.
You will need to make the soup in batches. Place tomatoes, coarsely chopped cucumber, jalapeño, cilantro sprigs, garlic, vinegar, and olive oil in a blender with 1 1/2 teaspoons salt and some pepper. Purée until the soup is completely smooth. Strain the soup and taste for seasoning. Repeat with the rest of the soup ingredients. Chill the soup in the refrigerator; it should be served very cold.
Toss the diced pepper, diced shallots, and diced cucumber together in a small bowl. Pour the gazpacho into six chilled soup bowls, and scatter the pepper mixture over the soup. Season the cherry tomatoes with salt and pepper. Finish each soup with a drizzle of really nice olive oil.
To serve family-style, place the soup in a chilled tureen or pretty pitcher and garnish with the tomato halves and cilantro; pass the diced vegetables on the side.