What a fantastic question! Unfortunately, I started writing something for you and realised that there is just no chance I can give you a quality answer in the time I have this weekend, but I also didn't want to leave you hanging with nothing. That's because it's quite difficult to give you such a quality oversight of such a diverse region over such a long time period. What I can do is offer you some other answers of mine you might find interesting:

• I've done two podcasts about the British Caribbean's history with a focus on black experience. In #59, I talk about the end of slavery and its aftermath; in #104 I talk about resistance and rebellion in Jamaican history. The second one focuses very heavily on slavery but resistance to it, and also talks about one of the most important moments of resistance post-emancipation.
• I have this 7-part answer on the political history of Bermuda, which after the opening context starts with an exploration of Bermuda's movement to end racial segregation.
• From this answer, this answer and this answer you can piece together some other key moments in the history of the region.

And in the way of some quickfire reading suggestions:

• Gad Heuman, The Caribbean (2006).
• Thomas Holt, The Problem of Freedom: Race, Labor, and Politics in Jamaica and Britain, 1832 - 1938 (1992).
• Hilary Beckles and Verene Sepherd, Caribbean Freedom: Economy and Society from Emancipation to the Present (1996).
• Kathleen Monteith and Glen Richards, Jamaica in Slavery and Freedom: History, Heritage and Culture (2002).
• O Nigel Bolland, On the March: Labour Rebellions in the British Caribbean, 1934 - 1939 (1995).
• Constance Sutton, Revisiting Caribbean Labour: Essays in Honour of O. Nigel Bolland (2005).
• Susan Craig-James, The Changing Society of Tobago, 1838 – 1938: A Fractured Hole (2008).
• Howard Temperley, British Antislavery 1833 - 1870 (1972).
• Mimi Sheller, Democracy After Slavery: Black Publics and Peasant Radicalism in Haiti and Jamaica (2000).
• Mary Turner, From Chattel Slaves to Wage Slaves: The Dynamics of Labour Bargaining in the Americas (1995).
• Gad Heuman, ‘The Killing Time’: The Morant Bay Rebellion in Jamaica (1994).
• Alvin Thompson, In The Shadow of the Plantation: Caribbean History and Legacy (2002).
• Richard Hart, Time for a Change: Constitutional, Political and Labour Developments in Jamaica and Other Colonies in the Caribbean Region (2004).
• Trevor Munroe, The Politics of Constitutional Decolonisation: Jamaica, 1944 - 1962 (1972).
• Ronald Hyam, Britain's Declining Empire: The Road to Decolonisation, 1918 - 1968 (2002).