Florence imitating Manhattan? Sullivan at the Uffizi, Alberti on Broadway? What if it was time we took such curious intuitions seriously? They whisper of invisible, enigmatic connections that make cities simultaneously unique and collaborative, unlike our generic-looking modern megapolises. How can we bring these cities back around to the stubborn and as yet unfulfilled pursuit of an ideal: connectivity between cities? To help solve this riddle, this bracing, scholarly essay combines urban history, aesthetics, and architectural theory, halfway between the cities of our dreams and the ones we live in.