Heat 1 T evoo, add minced garlic and shallots; Cook until soft. Stir in tomatoes, wine, water, chile, basil, orange zests, and 2 teaspoons salt. Bring to a boil then reduce heat and simmer gently until slightly thickened, about 15-20 minutes.
Use a kitchen mallet to pound both sides of calamari bodies to tenderize. Cut crosswise into rings. Add calamari and caper berries to sauce. Cook until calamari are opaque, about 2-3 minutes. Remove from heat.
Heat remaining 3 T evoo in a different skillet. Rub bread with garlic clove. Add clove to oil and cook 2 minutes. Add bread and fry, flipping once. Put bread in bowl, top with calamari sauce. season with pepper and basil.