In terms of seaborne contacts of Vietnamese court with foreign countries had two directions in the 19th century. One was with Island Southeast Asian ports such as Singapore, Malacca, Penang, Batavia, and Manila. The other direction was to Canton. The Canton contact of Vietnam again can be interpreted as one of the two directions of Vietnamese contact with China. The inland route far to Beijing was based on the political and diplomatic consideration, while the closer route to Canton by the court vessels was more for the economic consideration as the case for the contact with the Island Southeast Asia. In this article, author discusses three issues to illuminate the nature of the trips of the court vessels of the Nguyễn dynasty to Canton. First is to clarify detail itinerary of the trip from the Thuận An Estuary to the City of Canton via Đà Nãng and Hanan. Unlike to the Western ships that visited Canton but anchored at the Huang Fu, Vietnamese square-rigged/copper-bottomed ships sailed up the Pearl river to the Guangzhou city front to stay for four or five months before they returned to Vietnam. In the second chapter, various kinds of observation of the Vietnamese officials are discussed. If the objects of the observation are divided into two categories, one is the world Westerners in Canton, and the other is the world of Chinese. In a same place, Canton, the Vietnamese officials could have enough chance to compare the two worlds clearly. An important consequence for the Vietnamese officials was to conclude that the mechanical technology of the Westerners was better than that of Chinese. This kind of conclusion led the Vietnamese court to send court personnels to learn Western technologies and languages in the port cities of Island Southeast Asia and to enlarge contacts with them. In the last chapter, author tries to find out the items that the Vietnamese mission purchased in Canton in exchange to the Vietnamese products. The items that the Vietnamese mission purchased included ceramics, silk, books, and medicines. With the support of the Chinese settlers in Vietnam the mission was able to be involved in the deal of illegal items such as opium, and possibly some kinds of precious ginseng from Korea. Overall, the process of the itinerary, observation, and purchase during the trip to Canton was the way to form the new point of view of Vietnamese intellectuals towards China standing from the side of Westerners. To the Vietnamese who experienced both Canton/Macao and the Western worlds in the port cities of Island Southeast Asia China was not the only center of the world, nor the Westerners could be looked down as the barbarians. In Canton, a peripheral region looked from the imperial capital Beijing, but the most internationalized city of China at that time, Vietnamese officials were training themselves to overcome China.