The paper investigates the principal architectural considerations that governed the evolution of Madras, Bombay, and Calcutta, the three British colonial port cities of India, and seeks to answer the question of whether and to what extent these cities were planned. The extreme view in this debate on planning is taken by Sten Nilsson in his European Architecture in India, where he claims that the cities were based on strict symmetrical grid planning and were inspired by the Renaissance urban ideal, unlike traditional "organic" Indian cities. The paper questions this in view of the clear evidence that the British East India Company, unlike the French, was hostile to any ambitious urban planning on the part of the settlements. The hypothesis is further strengthened when one analyzes the ground plans of these cities, which show that defense considerations discouraged any symmetrical central planning, even though the streets were laid out in straight lines. In the absence of a central planning code, like the Royal Ordinance of 1573 for Spanish colonies, the building projects proceeded from the growing urban requirements of these settlements. The projects themselves were modest and defense naturally dominated building activities, mainly because these tiny enclaves were surrounded by hostile local and European powers. The growing needs of the inhabitants could not be neglected, however, and churches and hospitals came next in order of priority. The governors' mansions, on the other hand, had a position of peculiar importance in these port cities as they were meant to be a clear and visible symbol of authority. Not least interesting in these conurbations was the confluence of two traditions, Western and Eastern, though it must be added that the predominant style tended to be European, and mostly contemporary Tuscan. The conclusion reached is that while there was hardly any grandiose, symmetrical, total planning in these port cities, the city fathers did not neglect to make them habitable and even pleasant by developing gardens and parks in them.