This website looks at three distinct cases, spanning over 200 years of history, to show that while the Caribbean region shares commonalities that link them to each other it is their distinctiveness that prevents us from homogenizing the entire region into one singular border
Cuba

Johnson, Alvin Jewett. Johnson’s Cuba, Jamaica and Porto Rico. undated 1862.
San Andres y Providencia

Hispaniola

http://maps.bpl.org. English: Author: Bowen, Emanuel. May 5, 2010.
“The Caribbean is a place where external definitions frequently transcend simple geography and socio-political boundaries and can be understood by both temporal and cultural categories”
– Marco Meniketti, Director of the Institute for Advanced Interdisciplinary Caribbean Studies in San Jose University