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I would recommend a read through Janet Abu-Lughod's book, Before European Hegemony. This covers trade routes and practices in different areas of the world during the late 14th through early 16th centuries. The remainder of this answer is pulled in great part from what I understood of the book. Water ways are preferred due to a lower rate of banditry. While ...


The Manila Galleon might be a contender if you add the overland and transatlantic parts of the trip. Manila to Acapulco or Panama, Panama to Havana, Havana to Seville. Do you count the round trip, if each leg waits for once-a-year seasonal winds?

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