Season 1 of Caribbean Life premiered on January 1, 2014.

Season 2 of Caribbean Life premiered on January 1, 2015.

Season 3 of Caribbean Life premiered on March 1, 2015.

Season 4 of Caribbean Life premiered on January 1, 2016.

Season 5 of Caribbean Life premiered on February 21, 2016.

Season 6 of Caribbean Life premiered on September 11, 2016.

Season 7 of Caribbean Life premiered on January 1, 2017.

Season 8 of Caribbean Life premiered on March 5, 2017.

Season 9 of Caribbean Life premiered on July 16, 2017.

Season 10 of Caribbean Life premiered on September 3, 2017.

Season 11 of Caribbean Life premiered on April 8, 2018.

Season 12 of Caribbean Life premiered on July 15, 2018.

Season 13 of Caribbean Life premiered on September 2, 2018.

Season 14 of Caribbean Life premiered on October 21, 2018.

Season 15 of Caribbean Life premiered on January 1, 2019.

Season 16 of Caribbean Life premiered on March 24, 2019.

Season 17 of Caribbean Life premiered on May 19, 2019.

Season 18 of Caribbean Life premiered on October 20, 2019.

Season 19 of Caribbean Life premiered on February 12, 2020.

Season 20 of Caribbean Life premiered on May 3, 2020.