V. S. Naipaul, a Caribbean writer of Indian ancestry is a renowned travelogue writer. He has travelled all across the globe and has written prolifically. He travelled India thrice purposefully and documented his experiences coloured with his personal biases. His writings on India show interplay of consistency and self-divergence: his preoccupations remain constant, while the response they produce is subject to change. In the first book, he took the role of a prophet of doom, and showcases his apathy to the country. In the second book also he is found to be forecasting an impending chaos in Indian civilization satirizes the progress of Indian self-rule. In the third travelogue, however, Naipaul is reborn into a new persona: accepting and tolerant. The paper endeavours to explore the ability of the writer to see penetrate into the socio-political scenario of a people and inability to give a final version of his Vision of India due to his position of an insider cum outsider viewer. Key Words: India, travel, culture, change, chaos, vision