Christopher Columbus, on reaching the Lesser Antilles, sights a rugged island on November 3 that he names Dominica (Latin for Sunday), an island peopled by Caribs; …

…later on the same day, he lands at Marie-Galante, which he names Santa María la Galante.

Among Columbus’s crew are young Spanish soldier Diego Velázquez de Cuellar, and Juan Ponce de León, who as a teenager had joined Spanish forces that eventually defeated the Moors of Granada.

Also aboard is Spanish navigator and geographer Juan de la Cosa, who draws the earliest surviving map showing the discoveries in the New World.

After sailing past Les Saintes (Los Santos, "The Saints"), …

…Columbus arrives at the island of Guadeloupe, which he names Santa María de Guadalupe de Extremadura, after the image of the Virgin Mary venerated at the Spanish monastery of Villuercas, in Guadalupe, Cáceres, Spain.

He explores this island from November 4 to 10.

The earliest settlers on Guadeloupe, who had arrived around 300 BCE and developed agriculture on the island, had been removed by the more warlike Caribs, who called the island "Karukera," which is roughly translated as "island with beautiful waters."

They are also the tribe to meet all of the later settlers to the island.

On Guadeloupe, Columbus is offered pineapple, which originated in South America, perhaps in the Parana-Paraguay basin, spread through much of the continent's lowlands and other tropical areas, and had probably been introduced to the Antilles by the Caribs.

Michele da Cuneo, Columbus' childhood friend from Savona, sailed with Columbus during the second voyage and wrote: "In my opinion, since Genoa was Genoa, there was never born a man so well equipped and expert in the art of navigation as the said lord Admiral."

Columbus named the small island of "Saona ... to honor Michele da Cuneo, his friend from Savona."

The same childhood friend reported in a letter that Columbus had provided one of the captured indigenous women to him.

He wrote, "While I was in the boat, I captured a very beautiful Carib woman, whom the said Lord Admiral gave to me.

When I had taken her to my cabin she was naked—as was their custom.

I was filled with a desire to take my pleasure with her and attempted to satisfy my desire.

She was unwilling, and so treated me with her nails that I wished I had never begun.

But—to cut a long story short—I then took a piece of rope and whipped her soundly, and she let forth such incredible screams that you would not have believed your ears.

Eventually we came to such terms, I assure you, that you would have thought that she had been brought up in a school for whores." (Cohen, J.M. (1969). The Four Voyages of Christopher Columbus. NY: Penguin. p. 139)

The exact course of Columbus' voyage through the Lesser Antilles is debated, but it seems likely that he turned north, sighting and naming several islands, including Montserrat (for Santa María de Montserrate, after the Blessed Virgin of the Monastery of Montserrat, which is located on the Mountain of Montserrat, in Catalonia, Spain); …

… Antigua (after a church in Seville, Spain, called Santa María la Antigua, meaning "Old St. Mary's"): …

… Redonda (Santa María la Redonda, Spanish for "St. Mary the Round", owing to the island's shape); …

…Nevis (derived from the Spanish Nuestra Señora de las Nieves, "Our Lady of the Snows", because Columbus thought the clouds over Nevis Peak made the island resemble a snow-capped mountain); …

…Saint Kitts (for St. Christopher, patron of sailors and travelers); …

…Sint Eustatius (for the early Roman martyr, St. Eustachius), both of which have been long occupied by a substantial Carib population; …