Christopher Columbus (or Cristóbal Colón, as the Spanish knew him) sailed through the Virgin Islands in November 1493 during his second voyage to the New World. The admiral’s first voyage in 1492 had taken him to the Bahamas, Cuba, and Hispaniola. On Christmas Eve, 1492, his flagship, the Santa Maria, grounded on a reef and sank off Hispaniola. Columbus and his men salvaged what they could from the ship to build a settlement for the 40 men he would have to leave behind at what he called La Navidad.

The aim of Columbus’s second voyage was settlement. Seventeen ships and more than 1,000 men departed the Canary Islands on October 13, 1493. The fleet made good time across the Atlantic and spotted the island of Dominica on November 3, 1493. They sailed northward along the northern Leeward Islands until November 13, when they reached a large, fertile, and well-populated island that Columbus decided to name Sancta Cruz (The Holy Cross).

Columbus sent some of his men ashore at Salt River Bay for freshwater and, some reports claim, to capture natives who could tell him where he was. When the advance party was returning to the fleet, it encountered a canoe carrying four Carib men, two Carib women, and two Taino slaves. A fight between the two parties ensued; Columbus’s men overturned the canoe while the Caribs peppered the Europeans with poison arrows. Columbus’s party was impressed by the Caribs’ prowess as warriors. Columbus’s son, Don Fernando, wrote later about one Carib who kept shooting after the canoe was upset “as if he had been on dry land.”

Columbus named the area in front of Salt River Bay the Cape of Arrows after the skirmish. In the end, one member of Columbus’s party died, and one Carib was killed. The rest of the native party was taken as prisoners and eventually transported to Spain. It was, no doubt, a terrible fate for these captured people. A glimpse of their treatment is given by Columbus crewman Michele de Cuneo, who recorded matter-of-factly the details of his sexual assault on “a very beautiful Carib woman whom the Lord Admiral gave to me.”

After the skirmish at St. Croix, Columbus divided his fleet; the small caravels, including the one in which he rode, sailed northward through what is now Drake’s Channel. As he sailed, Columbus was impressed by the number of small islands before him and named them Las Virgenes after the then-popular myth of St. Ursula and her 11,000 virgin martyrs killed by the Huns. St. Ursula remains on the official seal of the British Virgin Islands. The second half of Columbus’s fleet remained south and sailed straight for the eastern end of Puerto Rico, where the two parties met up and continued on their way to Hispaniola.

Although Columbus did not stop to explore these islands, he did name many of them. During the passage he named Virgin Gorda (Fat Virgin) and gave Tortola the name Santa Ana, which did not stick.

Other early explorers passed through the islands but did not settle. Ponce de Leon led voyages in the area in the early 16th century; Sir Sebastian Cabot and Sir Thomas Pert passed through in 1517 after exploring Brazilian waters. Sir John Hawkins sailed through in 1563 with his first cargo of African slaves for Hispaniola. On a third voyage, Hawkins sailed with young Francis Drake. Later, after being knighted, Drake returned to the Virgin Islands in 1585, where he mustered his fleet in North Sound, Virgin Gorda, that same year for a disastrous attack on the Spanish settlement on Puerto Rico. The main passage through the island group now bears Drake’s name. Eleven years later, the Earl of Cumberland used the same North Sound as a staging area for a more successful attack on Puerto Rico.