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The Bay and the Islands of Colonia del Sacramento represent the region of the Portuguese settlement, which is under UNESCO list of World Cultural Heritage since December 6, 1995. At the same time it would add to the existing zone, a reservoir of historic testimonies of the rural life. The area forms, as a whole, a singular example of the daily colonial life carried out in the sea, the city and the country. The geographical area within the Bay and the Islands entails some of the richest aspects of the maritime history in South America. The West direction that the coast takes in relation to the continent, motivated—in the first years of the sixteenth century—the search for an inter-oceanic connection through De La Plata River and the first sea settlements of America, specifically in the mentioned area. From the consideration of Tordecillas Treaty, an increase in the sea traffic and maritime occupation mainly occurred by the Portuguese and Spanish but also by the incipient English and Dutch fleets. In the Bay and Islands the first maritime settlements form up in the zone and the first anchorage and shipyards are prepared. Architectonic testimonies of those moments are found in San Gabriel Island. Several shipwrecks that the bay holds contribute to document this historical process. Some of them belong to certain stages of the discovery and others give evidence of commercial activities that allow De La Plata River to abandon, from 1680, its condition of marginal area to become an active commercial region. As a consequence of the foundation of Colonia del Sacramento, this area becomes an active commercial area maintaining the tradition of maritime bastion and the access to the southern continent of America.