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1.
An alcoholic beverage which is made by mixing half orange juice and half Shock Top beer, with a shot of pineapple rum. The Island Hopper was invented by an anonymous U.S. Marine somewhere in a Southern California bar, and is named in honor of the Marines who fought in the Pacific in World War II. (the "Island Hopping Campaign" as it was called.)
Lance Corporal Hernandez: "Dude Corporal Clark just bought a round of fucking delicious drinks. What is this tropical taste-bud wonder?"

Lance Corporal Bondarenko: "It's a fuckin Island Hopper. You know, like in World War II. Good shit I know."

Corporal Clark: "That bartender chick is hot as fuck...imma buy her an Island Hopper!"
by CPgrunt03 February 01, 2013
 
2.
A woman who teases many men by flirting with them and not making up her mind as to who she likes.
"Hey! She was just flirting with me yesterday!"..."Yea dude she's an island hopper."
by W1LDC4RD October 15, 2006
 
3.
Puerto Ricans who have hopped over into the U.S.
My friend Tanya thinks she's special for being an Island Hopper!
by shaze August 25, 2006