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Cartagena (Colombia)

Caribbean for History Buffs: 12 Sites to Explore the Region’s Past

Cartagena (Colombia)
Editor
Jorge Oliver

Last updated
Nov 30, 2023

Sailing to the Caribbean isn’t just embarking on a journey to tropical paradise; it can also feel like traveling back in time.

From pre-Columbian marvels to the oldest colonial cities in the Americas, the region is a living historical museum of UNESCO World Heritage Sites. History buffs have plenty of opportunities to geek out on the Caribbean’s storied, often complex and always fascinating past.

What’s more, most historical sites can be easily explored on a shore excursion or independently. Better still, some are well within walking distance from your cruise ship. Here are 12 of our favorite Caribbean attractions that offer a window to the past.

And if you want more Caribbean cruising tips, check out our best Caribbean cruise content, itineraries, reviews and more.

1. Old San Juan, Puerto Rico

San Juan (Photo:Gary Ives/Shutterstock)
San Juan (Photo:Gary Ives/Shutterstock)

One of the busiest cruise ports in the Caribbean also happens to be home to one of the region’s most historically-rich destinations. Dating back to 1521, Old San Juan places visitors firmly in the Spanish colonial era with its city walls and bastions, cobblestoned streets, charming plazas, centuries-old churches (including Saint John the Baptist Cathedral, the second-oldest cathedral in the Americas) and museums.

The ocean-facing 17th-century fortifications of San Felipe del Morro and Castillo San Cristóbal are Old San Juan’s most popular attractions, and beautiful sights to witness from your ship while sailing in or out of San Juan Bay. But wandering through the city’s history-soaked streets is every bit as alluring.

2. Chichén Itzá, Mexico

Chichen Itza (photo by Shutterstock)
Chichen Itza (photo by Shutterstock)

The legacy of the Maya civilization dominates the Yucatan Peninsula, and hundreds of archaeological sites dot the low-laying landscape in this unique region that covers portions of Mexico, Guatemala and Belize. But among the many options, Chichén Itzá stands on a league of its own.

The complex boasts the distinction of being Mexico’s second most-visited archaeological site, and its iconic Temple of Kulkulcán was voted one of the New Seven Wonders of the World in 2007. As one of the largest Maya cities, Chichén Itzá was built over a period of 2,700 years and houses more than 20 building groups.

Aside from Kulkulcán, other noteworthy structures include El Caracol observatory, the Great Ball Court, the Tzompantli skull platform, and the Temple of the Warriors. Located in the heart of the Northern Yucatan Peninsula, cruisers can most easily access the archaeological complex from Progreso, but it’s also within reach from Playa del Carmen.

3. Historic Bridgetown and its Garrison, Barbados

Parliament Building in Bridgetown, Barbados (Photo: Jorge Oliver)
Barbados' Parliament Building in Bridgetown (Photo: Jorge Oliver)

Barbados recently became a parliamentary republic within the British Commonwealth, shedding its allegiance to the monarchy of the United Kingdom. But evidence of the island’s English history lives on, particularly in the capital city of Bridgetown.

Built in the 19th-century, the neo-Gothic Parliament Buildings are strikingly reminiscent of Britain’s Victorian Era architecture. Just outside the heart of the Bajan capital, the Garrison Historic Area unlocks more past relics for visitors. Saint Ann’s Fort, an 18th-century military building that today houses the Barbados Defence Force, is the centerpiece of the Garrison.

But the showstopper is the building commonly known as George Washington House, an historic house where the first U.S. president stayed in 1751 when he was just 19 years old. This anecdote makes Barbados the only country outside the present United States that Washington visited.

4. Saint-Pierre, Martinique

Martinique (Photo:Pack-Shot/Shutterstock)
Martinique (Photo:Pack-Shot/Shutterstock)

Once upon a time nicknamed ‘The Paris of the Caribbean,’ the seaside town of Saint-Pierre in Martinique can also be considered a Pompeii of the tropics.

As the former capital of the present-day overseas department and region of France, Saint-Pierre thrived culturally and economically until the nearby volcano Mount Pelée erupted in 1902, killing 30,000 residents and burying the town in pyroclastic flow.

The aptly-named Memorial de la Catastrophe de 1902 museum offers a comprehensive account of the natural disaster. But simply walking around the rebuilt town also reveals the haunting ruins frozen in time, including what’s left of the Grand Theater, the church of Fort de Saint-Pierre or the Figuier barracks.

5. Cartagena, Colombia

View of Cartagena's Plaza de los Coches square and Torre del Reloj gate (Photo: Jorge Oliver)
Cartagena's colonial charm is one of the main attractions of this Colombian city (Photo: Jorge Oliver)

It’s easy to forget that the Caribbean isn’t just made up of islands. And on mainland South America, the Colombian coastal city of Cartagena is one of the Caribbean’s most alluring destinations.

More than seven miles of walls and bastions surround the old town of Cartagena, holding the colonial treasures that lie within. The city’s charming plazas, narrow streets, multiple churches and fascinating museums tell the story of what became the main trade port between Spain and its vast colonial empire.

Just outside of the city gates, the sprawling Castillo San Felipe de Barajas fortress looms large, evidence of Spain’s determination to repel enemy attacks from rival colonial powers, while the trendy neighborhood of Getsemaní attracts visitors with its vivid murals, live music venues, bars and restaurants.

6. Christiansted National Historic Site, St. Croix

Fort Christiansvaern in Christiansted, St. Croix (Photo: USVI Department of Tourism)
Fort Christiansvaern is the centerpiece of St. Croix's Christiansted National Historic Site(Photo: USVI Department of Tourism)

Although St. Thomas’ Charlotte Amalie is the capital of the US Virgin Islands and is home to noteworthy remnants from the island’s colonial past, Christiansted in neighboring St. Croix carries stronger historical significance.

The Crucian city served as the capital of the Danish West Indies (yes, even Denmark had colonies in the Caribbean), and the Nordic nation’s influence here is ubiquitous. Built in 1749, the mustard-hued Fort Christiansvaern is the centerpiece of the six-acre Christiansted National Historic Site, which also includes architectural relics like the Steeple Building, the Customs House, the Lutheran Church, and the Danish West India and Guinea Company Warehouse.

Elsewhere in town, you’ll also find the living legacy of Christiansted’s unique mix of 18th-century Danish architecture and tropical touches.

7. Brimstone Hill Fortress, St. Kitts

Brimstone Hill Fortress in St. Kitts (Photo: Jorge Oliver)
Brimstone Hill Fortress National Park is one of the main attractions in St. Kitts (Photo: Jorge Oliver)

Imposing fortifications were not just a Spanish specialty in the Caribbean. Built by the English in the 18th century on the island of St. Kitts, Brimstone Hill Fortress still stands as one of the best-preserved citadels in the Americas and is the most extensive British military fortification in the Western Hemisphere.

The complex also boasts an enviable location on a steep 750-foot hill overlooking the Caribbean Sea on the northwest coast of the island, a strategic military setting that earned the site the moniker “The Gibraltar of the Caribbean.” A National Park since 1987 and a UNESCO World Heritage Site since 1999, Brimstone Hill Fortress is located only 30 minutes away from Basseterre’s Port Zante, the island’s cruise port, making the site an easily accessible day tour for cruisers.

8. Tulum, Mexico

Tulum, Mexico. God of Winds Temple overlooking the Caribbean Sea (Photo: emperorcosar/Shutterstock)
Mayan ruins overlooking a beach in Tulum, Mexico (Photo: emperorcosar/Shutterstock)

Located where the Yucatan Peninsula meets the Caribbean Sea, the Mexican state of Quintana Roo is brimming with jaw-dropping Mayan archaeological sites dating back centuries. But in terms of wow factor, few can rival the magnificent ruins of Tulum.

Set on a cliff against the backdrop of the glimmering waters of the Caribbean, Tulum was one of the last cities built and inhabited by the Maya. The 25-feet-tall El Castillo pyramid is Tulum’s most impressive sight, but other buildings – such as the God of the Winds Temple, the Temple of the Frescoes and the Temple of the Descending God – equally contribute to the Mayan city’s beauty and mystique.

The site is most easily accessible from Playa del Carmen, but you can still plan a visit even if your ship calls in Costa Maya or Cozumel.

9. Colonial City of Santo Domingo, Dominican Republic

Santo Domingo

Founded in 1496, Santo Domingo is not just the first site built by Spanish in the Caribbean; it’s the oldest continuously inhabited European settlement in the Americas.

It’s no wonder that the Dominican capital is often referred to as the ‘city of firsts,’ as it became the site of the first cathedral, monastery, university, hospital and other important institutions in the so-called New World.

Santo Domingo’s Zona Colonial sits just west of the mouth of the Ozama River and facing the Caribbean Sea, and is home to important landmarks like the Alcázar de Colón palace, Ozama Fortress, Puerta del Conde city gate and Santa María la Menor Cathedral. The colonial city’s checkerboard grid pattern became the blueprint for Spain’s numerous settlements across the Americas.

10. Nelson’s Dockyard, Antigua

Maritime museum in Nelson's Dockyard, Antigua (Photo: Jorge Oliver)
Nelson's Dockyard in the southern coast of Antigua (Photo: Jorge Oliver)

On the southern shore of the island of Antigua in English Harbour, Nelson’s Dockyard gives visitors a glimpse into 18th century life in the Caribbean.

Named after famed English admiral Horatio Nelson, who lived in Antigua in the 1780s, this heritage site was built in the mid-18th century as a naval ship repair station. It soon grew to become a naval village, and today functions as a mixed-use site that houses a museum, two hotels, craft and food shops, restaurants, and a large marina.

Don’t miss a visit to nearby Shirley Heights on the Shekerley Mountains, part of Nelson’s Dockyard complex and where you can visit a comprehensive exhibit on the island’s history and enjoy panoramic views of English Harbour.

11. Historic Willemstad, Curacao

Curacao (Photo:Sorin Colac/Shutterstock)
Curacao (Photo:Sorin Colac/Shutterstock)

Have you visited Dutch gables on a Southern Caribbean cruise? Curacao’s capital city of Willemstad looks and feels like a colorful slice of Amsterdam in the tropics. But the appearance isn’t just cosmetic: as a constituent country in the Kingdom of the Netherlands, Curacao’s ties to the European nation run deep.

Willemstad dates back to 1634, with most of its historical landmarks concentrated in the district of Punda. Highlights include the candy-colored facades of the Handelskade waterfront; Fort Amsterdam, which doubled as a military base and the headquarters of the Dutch West India Company; and Mikvé Israel-Emanuel, the oldest surviving synagogue in the Americas.

12. Hamilton House, Nevis

Alexander Hamilton's birthplace in Nevis (Photo: Jorge Oliver)
Alexander Hamilton's house is one of the main historical attractions in Nevis (Photo: Jorge Oliver)

U.S. history buffs (and Lin Manuel Miranda fans) know that American statesman and founding father Alexander Hamilton was born not in the former Thirteen Colonies but in the sleepy Caribbean island of Nevis instead. Unsurprisingly, the Georgian-style stone building is the most visited attraction on the island.

Though modest, Hamilton House offers visitors a unique slice of Caribbean history. The first floor houses the Alexander Hamilton Museum and the Museum of Nevis History, with exhibits that chronicle the life and achievements of the first secretary of treasury of the United States, as well as displays about Nevisian history and culture. The second floor is the meeting space for the Nevis Island Assembly, the local legislative body.


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