The best books on the early modern global Caribbean

Who am I?

I am a historian of the early English Atlantic who began studying New England but soon turned to the Atlantic more generally and the Caribbean in particular. All the aspects of 17th century Atlantic history that most intrigue me played out in the Caribbean. A fascinating and complicated place, the West Indies—although claimed by the Spanish as their exclusive purview—became diverse, witness to a variety of interactions. I’m particularly interested in works that allow us to see these changes in the period when the region was a global meeting place undergoing vast shifts. Much excellent scholarship explores the later era of sugar and slaves, of major imperial wars, of movements for independence and emancipation. What interests me most is the period before that, when the region was being transformed into a crucible of global transformation.


I wrote...

English Conquest of Jamaica: Oliver Cromwell's Bid for Empire

By Carla Gardina Pestana,

Book cover of English Conquest of Jamaica: Oliver Cromwell's Bid for Empire

What is my book about?

In 1655, England attempted to conquer Spanish America. Believing that Spain was weak and that the African and Native residents of its American lands longed to be liberated from Spanish oppression, the English expected to conquer vast lands. They failed in this ambitious agenda for many reasons, not the least because of the unrealistic nature of their expectations.

This book chronicles those expectations, the preparations that went into the campaign, its humiliating failure on the poorly defended island of Hispaniola, and its limited but nonetheless significant results. Jamaica, taken as a place where the demoralized and sickly force could regroup, proved difficult to conquer; it was five years before the Spanish residents ended their resistance to the English invasion. Despite an inauspicious beginning, Jamaica emerged as Britain’s most valuable colony. 

Shepherd is reader supported. When you buy books, we may earn an affiliate commission.

The books I picked & why

Book cover of Atlantic Africa and the Spanish Caribbean, 1570-1640

Carla Gardina Pestana Why did I love this book?

David Wheat integrates Africa and Africans into the history of the Spanish Caribbean. Before I read this book, I knew that the Spanish relied more on native laborers than on Africans initially, and that their policies limited migration from Spain to Castilians of Roman Catholic heritage. Yet Wheat reveals how diverse and complex the early Spanish islands became, with Spanish from other regions not to mention Portuguese, Africans, and conversos (Catholics of Jewish heritage) intermixed with the approved migrants and the long-time indigenous residents.

By David Wheat,

Why should I read it?

2 authors picked Atlantic Africa and the Spanish Caribbean, 1570-1640 as one of their favorite books, and they share why you should read it.

What is this book about?

This work resituates the Spanish Caribbean as an extension of the Luso-African Atlantic world from the late sixteenth to the mid-seventeenth century, when the union of the Spanish and Portuguese crowns facilitated a surge in the transatlantic slave trade. After the catastrophic decline of Amerindian populations on the islands, two major African provenance zones, first Upper Guinea and then Angola, contributed forced migrant populations with distinct experiences to the Caribbean. They played a dynamic role in the social formation of early Spanish colonial society in the fortified port cities of Cartagena de Indias, Havana, Santo Domingo, and Panama City and…


Book cover of American Baroque: Pearls and the Nature of Empire, 1492-1700

Carla Gardina Pestana Why did I love this book?

Molly Warsh’s American Baroque perhaps best captures my point about the Caribbean as a global space. The book follows pearls harvested off the coast of Venezuela from the beds that produced them, through the enslaved divers who harvested them, the imperial officials who taxed them, the merchants who traded them, all the way to the consumers who valued them. It is a commodity history—a sort of history that often features the Caribbean region prominently—while at the same time offering a rich evocation of the many cultural aspects of the pearl’s role. Laborers who secreted pearls on their person to gain some of the wealth they produced and artisans who created lavish objects featuring pearls are as important to this account as the wealthy and powerful who displayed them in portraits of this era. 

By Molly A. Warsh,

Why should I read it?

1 author picked American Baroque as one of their favorite books, and they share why you should read it.

What is this book about?

Pearls have enthralled global consumers since antiquity, and the Spanish monarchs Ferdinand and Isabella explicitly charged Columbus with finding pearls, as well as gold and silver, when he sailed westward in 1492. American Baroque charts Spain's exploitation of Caribbean pearl fisheries to trace the genesis of its maritime empire. In the 1500s, licit and illicit trade in the jewel gave rise to global networks, connecting the Caribbean to the Indian Ocean to the pearl-producing regions of the Chesapeake and northern Europe.

Pearls-a unique source of wealth because of their renewable, fungible, and portable nature-defied easy categorization. Their value was highly…


Book cover of Creolization and Contraband: Curaçao in the Early Modern Atlantic World

Carla Gardina Pestana Why did I love this book?

The Dutch were a force to be reckoned with in the early modern Caribbean, trading with everyone and insinuating themselves everywhere. Rupert’s book shows how the small desert island of Curaçao became a trading entrepôt and in particular how Dutch suppliers, enslaved Africans, and Spanish consumers became entangled. One amazing aspect of this history that Rupert uncovered is the fact that the Protestant Dutch on Curaçao allowed the slaves there to be catechized by Spanish priests from the mainland (today’s Venezuela), working across not only imperial boundaries but also those of religion.

By Linda M. Rupert,

Why should I read it?

1 author picked Creolization and Contraband as one of their favorite books, and they share why you should read it.

What is this book about?

When Curacao came under Dutch control in 1634, the small island off South America's northern coast was isolated and sleepy. The introduction of increased trade (both legal and illegal) led to a dramatic transformation, and Curacao emerged as a major hub within Caribbean and wider Atlantic networks. It would also become the commercial and administrative seat of the Dutch West India Company in the Americas.

The island's main city, Willemstad, had a non-Dutch majority composed largely of free blacks, urban slaves, and Sephardic Jews, who communicated across ethnic divisions in a new creole language called Papiamentu. For Linda M. Rupert,…


Book cover of The Creole Archipelago: Race and Borders in the Colonial Caribbean (Early American Studies)

Carla Gardina Pestana Why did I love this book?

This new book realizes much of my wish to see histories of the Caribbean take seriously its importance as a site of diverse groups and unexpected exchanges. The Creole Archipelago focuses on five little-studied islands—Dominica, Grenada, St. Lucia, St. Vincent, and Tobago. Tessa Murphy reveals an interconnected maritime world, shaped by the use of canoes that allowed mobility free of the prevailing winds. Alongside consideration of the space itself and movement within it, Murphy explores the region’s diversity, its indigenous peoples, African, and Europeans of various stripes. She gives special attention to the indigenous peoples whose traditions, presence, and legacy determined much about these islands. In this watery borderland—a region within the larger Caribbean—interisland, intercolonial, and interimperial interactions were everyday occurrences.

By Tessa Murphy,

Why should I read it?

1 author picked The Creole Archipelago as one of their favorite books, and they share why you should read it.

What is this book about?

In The Creole Archipelago, Tessa Murphy traces how generations of Indigenous Kalinagos, free and enslaved Africans, and settlers from a variety of European nations used maritime routes to forge social, economic, and informal political connections that spanned the eastern Caribbean. Focusing on a chain of volcanic islands, each one visible from the next, whose societies developed outside the sphere of European rule until the end of the Seven Years' War in 1763, Murphy argues that the imperial frameworks typically used to analyze the early colonial Caribbean are at odds with the geographic realities that shaped daily life in the region.…


Book cover of Cannibal Encounters: Europeans and Island Caribs, 1492-1763

Carla Gardina Pestana Why did I love this book?

Boucher contributes to our understanding of two aspects of Caribbean history, the activities of French colonizers and the history of the Carib (or Kalinago) native peoples of the eastern Caribbean. Although Cannibal Encounters addresses imperial policies and warfare (in line with an older scholarship), it also reveals the importance of the indigenous peoples to the early interactions in the Caribbean basin. In particular, the rivalries between the French and the English played out in the context of confrontations, alliances, and betrayals involving the Kalinago.

By Philip P. Boucher,

Why should I read it?

1 author picked Cannibal Encounters as one of their favorite books, and they share why you should read it.

What is this book about?

Philip Boucher analyzes the images-and the realities-of European relations with the people known as Island Caribs during the first three centuries after Columbus. Based on literary sources, travelers' observations, and missionary accounts, as well as on French and English colonial archives and administrative correspondence, Cannibal Encounters offers a vivid portrait of a troubled chapter in the history of European-Amerindian relations.


You might also like...

The Lion and the Fox: Two Rival Spies and the Secret Plot to Build a Confederate Navy

By Alexander Rose,

Book cover of The Lion and the Fox: Two Rival Spies and the Secret Plot to Build a Confederate Navy

Alexander Rose Author Of Empires of the Sky: Zeppelins, Airplanes, and Two Men's Epic Duel to Rule the World

New book alert!

Who am I?

A long time ago, I was an early-aviation historian, but eventually realized that I knew only half the story—the part about airplanes. But what about airships? Initially, I assumed, like so many others, that they were a flash-in-the-pan, a ridiculous dead-end technology, but then I realized these wondrous giants had roamed and awed the world for nearly four decades. There was a bigger story here of an old rivalry between airplanes and airships, one that had since been forgotten, and Empires of the Sky was the result.

Alexander's book list on Zeppelin airships

What is my book about?

From the author of Washington’s Spies, the thrilling story of two rival secret agents — one Confederate, the other Union — sent to Britain during the Civil War.

The South’s James Bulloch, charming and devious, was ordered to acquire a clandestine fleet intended to break Lincoln’s blockade, sink Northern merchant vessels, and drown the U.S. Navy’s mightiest ships at sea. Opposing him was Thomas Dudley, an upright Quaker lawyer determined to stop Bulloch in a spy-versus-spy game of move and countermove, gambit and sacrifice, intrigue and betrayal.

Their battleground was the Dickensian port of Liverpool, whose dockyards built more ships each year than the rest of the world combined and whose merchant princes, said one observer, were “addicted to Southern proclivities, foreign slave trade, and domestic bribery.”

The Lion and the Fox: Two Rival Spies and the Secret Plot to Build a Confederate Navy

By Alexander Rose,

What is this book about?

From the New York Times bestselling author of Washington's Spies, the thrilling story of the Confederate spy who came to Britain to turn the tide of the Civil War-and the Union agent resolved to stop him.

"Entertaining and deeply researched...with a rich cast of spies, crooks, bent businessmen and drunken sailors...Rose relates the tale with gusto." -The New York Times

In 1861, soon after the outbreak of the Civil War, two secret agents-one a Confederate, the other his Union rival-were dispatched to neutral Britain, each entrusted with a vital mission.

The South's James Bulloch, charming and devious, was to acquire…


5 book lists we think you will like!

Interested in colonies, the economy, and Spain?

10,000+ authors have recommended their favorite books and what they love about them. Browse their picks for the best books about colonies, the economy, and Spain.

Colonies Explore 70 books about colonies
The Economy Explore 198 books about the economy
Spain Explore 186 books about Spain