In any case, Columbus first landed on Guanahani, which Columbus renamed San Salvador; it was an island in what is now The Bahamas, but there is still uncertainty about which present-day island Columbus actually landed. 1  He also discovered the islands of Cuba and Hispaniola on his first voyage before returning home. Columbus' second voyage conisted of 17 ships that included groups of prospective new colonists. Columbus became the first European to sight and name many of the islands of the Caribbean, including the following: Montserrat; Antigua; Redonda Nevis; Saint Kitts