I'd like to offer up another classic-era US commemorative coin that I previously held back, but merits strong consideration (IMO) for an "Island Connection" list: the 1892-93 World's Columbian Exposition - Christopher Columbus Half Dollar - I thought it might be the first coin to come to mind for collectors - but "No.". (Shows how much I know!)
Between 1890 and 1891, the US Congress authorized the World's Columbian Exposition ("Exposition") to be held in Chicago, Illinois and appropriated funds for its financial support. The Exposition was to celebrate "the four hundredth anniversary of the discovery of America by Christopher Columbus."
Reference to "America", however, was/is not interchangeable with "United States". Columbus' 1492 explorations were in the Caribbean Sea not the North American mainland that would come to include the United States. In fact, Columbus never stepped foot on mainland North America.
During Columbus' 1492 voyage, he visited an island in the present-day Bahamas that he named San Salvador. He also explored parts of Cuba and Hispaniola (the island that presently is comprised of Haiti and the Dominican Republic).
So, Columbus "discovering" America was really more about "discovering" Caribbean islands (and later areas of Central and South America) vs. the United States - and thus the coin's "Island Connection" is established.

Collecting history one coin or medal at a time! (c) commems. All rights reserved.