Start with high-confidence caribbean history books, then narrow by subgenre or adjacent topics.
Sweetness and Power
Sidney W. Mintz
Empire of Blue Water
Stephan Talty, John H. Mayer
Empire Unseen
Mélanie Lamotte
Jewish Pirates of the Caribbean
Edward Kritzler
Silencing the Past
Michel-Rolph Trouillot
History of the Upper Guinea Coast
Walter Rodney
Atlantic Africa and the Spanish Caribbean, 1570-1640
David Wheat
Try Not to Be Strange
Michael Hingston