During colonial times, an active maritime trade existed between Spain and the New World, with convoys sailing annually to and from Mexico and returning via Havana, Cuba, after wintering in America. A database constructed from secondary and open sources revealed that Spanish vessels were sailing over open waters along a northern path near Louisiana and a southern path across the central Gulf of Mexico. These routes were traversed in about one month and scheduling for the convoy was based on an understanding of the Americas' meteorological and oceanographic climate. However, other factors may also have been involved in the directional layout of the routes. Today these ancient routes crisscross planning areas for oil and gas lease sales in the US Exclusive Economic Zone and the information presented in this article may aid in identifying areas where historic shipwrecks may lie. Maps and documents found during this study helped piece together the evolution of our understanding of the Gulf of Mexico surface circulation and how this knowledge influenced sailing during colonial times. Keywords Routes Á Derrotas Á Gulf of Mexico Á Veracruz Á Havana Á New Spain Á Shipwrecks A. Lugo-Fernández (&) Physical Sciences Unit (MS 5433),