This paper will look at the passenger side of monsoon navigation through the eyes of the Mamluk-era traveler Ibn Battuta. Born and raised in Morocco, he started his travels with a caravan journey east-bound toward Mecca. Traveling to Upper Egypt and the Red Sea coast, he was prepared to sail across to reach his pilgrimage destination, but instead had to return to Cairo, and later reached Mecca by the land route. Ibn Battuta would have been well aware of boat traffic on the Mediterranean, but there is no indication that he had ever travelled by ship before venturing on pilgrimage in 1325. The paper focuses on the impact of Indian Ocean environment on sailing choices, opportunities and obstacles facing the voyager at three oceanic transit points: (1) between the Red Sea and the Arabian Sea, (2) mid-ocean, where the southern tip of the Indian subcontinent meets the island of Ceylon; and (3) sailing from India to the Far East. Ibn Battuta’s first sailing experience was impacted by the hajj calendar and the winds in the western part of the Indian Ocean. We can follow him along with the returning pilgrims to the eastern shores of Africa and coasts of southeastern Arabia. Navigation in the region, while regulated by the Northeastern (winter) and Southwestern (summer) monsoons, was also dependent on regional meteorology and currents. Shipping at the southern reach of the Indian subcontinent was complicated by the South-Asian landmass effect on the wind and rain regime. We are informed of the navigation practices on these routes by the later Arabic sources. Eastbound oceanic routes from such important ports as Calicut varied depending on the destination: shorter sailings to Ceylon or into the Bay of Bengal (both of them taken by Ibn Battuta) or further east toward China or Indonesia. Ibn Battuta is shipwrecked here, other vessels are borne away by powerful winds, and extended delays are imposed by the weather. Ibn Battuta’s narrative, while not chronologically precise, allows us to estimate the environmental impact on his itinerary and travel timeline, as we trace his maritime journey all the way to China.