How to Take a Caribbean Vacation — While Acknowledging Its Painful Past

What do you know about the history of your favorite Caribbean island? Or the previous lives of that luxurious seaside resort?

Conceptual illustration of an eye reflecting an island, used to illustrate a personal essay about considering colonialism in Caribbean travel experiences
Photo: Illustration by Michelle D'Urbano

St. Croix was showing off. At least, that's how it seemed last spring as I sat eating breakfast on the terrace of The Buccaneer, watching cotton clouds drift across the sky as bougainvillea blossoms quivered in the breeze. Below me, the U.S. Virgin Island was resplendent, its rolling hills — carpeted in green and punctuated with fruit trees and coconut palms — giving way to a white-sand coastline. It was a scene straight from a Caribbean tourism ad.

When the server came by to refill my coffee, I asked her the name of the beach in front of us, the centerpiece of this tranquil scene. "Gallows Bay," she said, before adding, "It's where they used to hang the slaves who tried to escape."

I've made a career out of my love for the Caribbean. I've championed the region through my writing and videos for more than 30 years. But even I — a Black woman of Jamaican and Bajan descent — have failed to acknowledge its painful past in my work. Now, with so many more of us fully aware of the centuries-long plight of Black people, those involved in the Caribbean tourism industry have an opportunity to take a critical look at how we're promoting our countries to visitors. Yes, we have the tropical trifecta of sun, sea, and sand. But like the United States, we also have a long and complex history of racial injustice — one that, even today, forms the scaffolding of the travel industry itself.

In the 18 months since the racial reckoning brought on by the murder of George Floyd, I have found certain cultural touchstones especially powerful. Among them was The Underground Railroad, a 10-part TV adaptation of Colson Whitehead's 2017 Pulitzer Prize–winning novel that imagined the 1800s-era network of abolitionists and safe houses for enslaved Africans in America as a real train. One scene displays an unimaginably brutal act against a Black man on the grounds of a plantation as, steps away, the white estate owners and their guests enjoy an elegant alfresco meal accompanied by joyful tunes performed by enslaved musicians.

That scene was stuck in my head as I checked in to The Buccaneer. The former sugar and cotton plantation was once known as Estate Shoys, and the first structure on the sprawling property was built in 1653. I felt an immediate and instinctual sense of unease as I looked over the ruins of colonial-era mills and buildings. It's not the first time I've experienced this disconnect between the beauty of my surroundings and the brutality that took place in their past.

That feeling could have come over me at any number of the Caribbean hotels that were once sugar estates, from Jamaica's Tryall Club to the cluster of plantation inns on Nevis. Between 1663 and 1807, Britain shipped more than 2 million Africans to the Caribbean to be sold as slaves. Descendants of those slaves—my ancestors—now make up the majority of the region's population. And modern tourism there, of course, has its roots in colonialism. After all, what were the overseas guests of those plantation owners if not the region's first tourists?

The Buccaneer has been a hotel since 1947, and according to the commemorative book published by the resort to celebrate its 70th anniversary, it was the first hotel on the island, run by the Armstrongs, an American family who had been using the property to raise cattle. When it opened, "guests, known as continentals, made a two-day trip from the mainland and often mixed their own drinks; helped rake the beach, painted furniture and planned meals," I read.

Thumbing the book's pages, I saw retro ads touting limbo dancing as entertainment and menus from 1955 that featured "native dishes planned for American palates." But there was no mention of the enslaved people who once lived on the property, only a reference to its having been a sugar factory in 1733 and a note that the sugar mill is now used for "candlelit dinners and blissful weddings." With three beaches, a golf course, and a staff I found to be warm and caring, The Buccaneer is a good choice for most visitors to St. Croix. But its history — and that of other plantations turned resorts — is inextricably tied to slavery and colonialism, and it shouldn't be dismissed, because the legacy of that history remains.

Check in to a typical Caribbean resort today and you'll find more dark-skinned employees working as waiters, housekeepers, and groundsmen than at the front desk, where lighter skin tones and longer, straighter hair are more often seen. At the management level, a marked majority are either white, or foreign, or both. And when was the last time you were served by a white employee in a Caribbean restaurant? With a few notable exceptions, marketing materials still show mostly white travelers being attended to by smiling Black staff. (At The Buccaneer, I couldn't help registering the novelty of having a young white guy from the Midwest serve me my sushi.)

We take tours of historic forts that center the experiences of the foreign officers who occupied them and are told about the lives of the privileged owners of great houses and plantations, yet learn little or nothing about the people who built and worked on them.

The fact is that many of us in the world of Caribbean tourism have had a hand in presenting this idyllic yet incomplete story of the region. I've been complicit myself, never before questioning the origins of the names of places like Gallows Bay.

I am thinking about all of it now.

In the past 18 months of traveling around the Caribbean I've found that, along with the delight I take in seeing new places, runs a vague but undeniable discomfort. For me — and perhaps other Black travelers — touring great houses, staying at former plantation homes, and even being in rooms with colonial-era décor feels unsettling. For my ancestors, the period offered neither elegance nor ease, only brutalization at the hands of the people they were forced to serve.

So how do we acknowledge and honor the region's difficult past while celebrating the places and people who have made it a magnet for millions of visitors? The Caribbean is a beautiful and culturally rich region, and I really want you to visit. But I want you to go with your eyes open. As you tour beautiful centuries-old buildings, I want you to be aware of their ugly past, because to ignore that heritage is to do the islands, the people, and yourself a disservice. Your Caribbean vacation needn't be a literal guilt trip, but it could be an opportunity to better appreciate the people who make it all possible.

I think there are things that we as conscious and respectful travelers can do better. To begin, consider staying in locally owned hotels so that your money goes straight back into the community. Some of my favorites: Pelican Beach Hotel, in the Turks and Caicos, and Grenada's Spice Island Beach Resort. I'd also encourage you to take longer trips (doable now since so many of us can work remotely) so that you have the time to do more than scratch the surface of a destination.

Eat at local restaurants and support local craftspeople by buying their products. For many years now, I've been doing the extra research and digging deeper, shopping for wood carvings at the Gallery of West Indian Art, in Montego Bay, Jamaica; handbags at Concalma, in San Juan, Puerto Rico; and silver bracelets at St. Croix's IB Designs, to name just a few.

Another thing we can do is support the spaces where history is preserved. A few months ago I visited Wade's Green Plantation, an 18th-century cotton and sisal estate on North Caicos that was once owned by a British loyalist. Unlike other Caribbean estates I've visited, this one has been left largely in ruins. So instead of following a tour guide through restored interiors to get a sense of colonial life, visitors have to use their imaginations and navigate the remains of the buildings on their own.

On a warm and cloudless spring morning last year, I stepped on crunchy brown leaves that carpeted what's left of the overseer's house, purposefully positioned so he could police the activities of the enslaved people nearby. For the first time I saw a cotton bush and picked my first boll, experiencing firsthand the painful burrs pricking my fingers as I tried to separate the fibers from the seeds and pod, and understanding how arduous the task of picking 860 acres of it must have been. I touched the limestone walls, hand-built by Africans who had to haul large boulders across the property, chip them flat, and stack them one by one. They were constructed without mortar or cement but have survived centuries — a tribute to the people who engineered them under the worst conditions.

At Wade's Green Plantation the realities of slavery and colonialism were not sensationalized, watered down, or romanticized. Yet I left simultaneously moved and in awe of the people who lived there and elsewhere in the Turks and Caicos, then and now. That tour left me with a deep respect for the Caribbean and its people. And in the end, isn't that what travel should be about?

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