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This image portrays the island hop of Christopher Columbus's second voyage to the Caribbean.

Island hopping is a term that has several different definitions as it is applied in various fields. Generally, the term refers to the means of crossing an ocean by a series of shorter journeys between islands, as opposed to a single journey directly across the ocean to the destination.

Island hopping, also called leap frogging, was an important military strategy in the Pacific Theater of World War II. The strategy employed by the Allies of World War II Combined Chiefs of Staff, beginning with Operation Cartwheel, was to bypass heavily fortified Japanese positions and instead concentrate the limited Allied resources on strategically important islands that were not well defended but capable of supporting the drive to the main islands of Japan. This strategy was possible in part because the Allies used submarine and air attacks to blockade and isolate Japanese bases, weakening their garrisons and reducing the Japanese ability to resupply and reinforce. Thus troops on islands which had been bypassed, such as the major base at Rabaul, were useless to the Japanese war effort and left to "wither on the vine."

Historically, airplanes that did not have the range to cross the Atlantic Ocean in a single flight took the "island hopping" route from the United States of America to Europe via the Caribbean and the Canary Islands or even further south via Brazil, Ascension Island, and Africa. A northerly route via Newfoundland, Greenland and Iceland was also possible.

Island hopping may also refer to the "hopping" from one island to another in an archipelago or multi-island nation. This may be done by means of air travel on a sort of puddle jumper or by boat or ferry. For example, tourism operators may invite visitors to enjoy an "island hopping adventure" by visiting the islands of the Bahamas.

In anthropology, island hopping is the method by which the Polynesian people settled the islands of the Pacific Ocean.

In biology, island hopping is the method by which plant and animal species colonize islands. Organisms will move or drift from one island to another and eventually become native to that region. Some species are only endemic to a small group of islands and never are able to "hop" to the mainland, as is that case with many birds of the Galápagos Islands.

In the computer security and intrusion detection field island hopping is the act of entering a secured system through a weak link and then "hopping" around on the computer nodes within the internal systems.

The Spanish discovery and conquest of the Caribbean was preceded by island hopping, as Christopher Columbus discovered San Salvador in 1492, Hispaniola and Dominica in 1493, and so on. He eventually went on to settle on, and name, most of the Caribbean islands. (See image above.)

• Kangaroo Route
• Extreme points of the World