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(covers information from several alternate timelines)
The term "Yankee traders" referred to American sailors of the 18th and 19th centuries who traveled Earth's oceans "in search of mercantile and territorial opportunity." 24th century Federation scholars compared the Ferengi to these ancient seafarers. (TNG: "The Last Outpost")
The holographic Leonardo da Vinci hypothesized that had been accosted by Spanish sailors and rendered unconscious to explain how he had arrived at the New World (which was actually an alien planet). da Vinci also claimed that the Portuguese were "mad sea dogs." (VOY: "Concerning Flight")
Commander Chakotay suggested that every sailor's nightmare was being becalmed in the middle of the ocean, similar to the isolated situation that the USS Voyager found itself in while traveling through The Void. (VOY: "Night")
Lieutenant Tom Paris wanted to be a sailor with the Federation Naval Patrol when he was a child, and even as an adult occasionally used terms like first mate and skipper, which he referred to as "sailor talk." (VOY: "Thirty Days")