The Age of Sail commonly refers to European endeavors after roughly 1450. However, two other examples of maritime efflorescence and decline occurred just before this. Early Ming imperial fleets and long-distance voyaging in Oceania relativize and throw into relief the contingency of the European accomplishment. After discussing these two examples, this article shows how they raise questions about the limits of an ocean basins framework and explores why Southeast Asia sits indistinctly between scholarly orientations that look predominantly westward across the Indian Ocean and eastward across the Pacific. In light of evidence that shows large oceangoing Southeast Asian ships were active in contemporaneous Indian Ocean networks, and in view of other features of the region’s maritime history, it suggests that attention to Southeast Asia’s connections with Oceania may merit further investigation.