Optimist International was was introduced to the English speaking Caibbean in Kingston, Jamaica in 1980.​
The First Optimist Club was the Optimist Club of Kingston, which was sponsored by the North Miami Beach Optimist Club of South Florida.  It was chartered with 48 members.  Its charter President was Andy Morgan.​
The First Female President was Jennifer Wynter in 1987.​

The First five clubs were chartered as follows:​
1980 Kingston OC​
1986 Montego Bay OC​
1986 Kingston Breakfast OC​
1987 Spanish Town OC​
1988 North St. Andrew OC  and St. Andrew OC​

Between 1980 and 1992 the clubs in the movement were apart of the South Florida District of Optimist International.​
With the establishment of 25 Optimist Clubs in 1992, the Jamaica District was born.  The District's first Governor was Theodore Golding.  The movement had by then spread to other Caibbean Islands including Barbados and Antigua.  The first Eastern Caribbean club was the Optimist Club of Bridgetown, Barbadoes which was sponsored by the OC of Montego Bay also in 1992.​

The First District Convention of the Jamaica District was held in Ocho Rios, St. Ann, Jamaica in 1993.  The District's first District Secretary/Treasurer was Dr. Ronald Bourne of the Spanish Town OC.​
On October 1, 1996 with 38 clubs in the movement from the region, the Caribbean District was born. The clubs were now spread more across the Caribbean region to now have clubs in Jamaica, Antigua, Barbados, St. Kitts, Montserrat, Dominica, Trinidad & Tobago, Grand Cayman, St. Lucia and Anguilla​
The First Governor of the District was Major Errol Alliman of the NorthSt. Andrew OC, his successor was Dudly Hall and his District/Secretary Treasurer was Gene M. Douglas.​

The first all female club was established by the North St. Andrew OC on September 28, 1999 and took the name the Barbican Pine OC.​

The First Female Governor of the Caribbean District was Shirley Jarrett October 1, 1999 to September 30, 2000.​

The First International Vice President from outside North America was Theodore Golding in 1990 to 2000, he also became the first non-caucasian and non Amercian to hold the office of International President for the tenure​
October 1, 2007 to September 2008.