Havana → Varadero (Cuba)

Havana stands as one of the oldest cities in the Americas, its streets lined with Spanish colonial architecture and relics of revolution. Varadero, by contrast, is a symbol of modern Caribbean tourism.

The Gateway to the Caribbean

The journey begins in Havana, where the shadows of the Spanish Empire still linger in stone fortresses and narrow streets. Once a critical hub for treasure fleets returning to Europe, Havana became both a jewel and a target—coveted by pirates and rival powers alike.

As you depart the coastline, the city fades into the vast blue, and ahead lies Varadero—its pristine beaches masking a deeper history of colonial wealth and later transformation into a global tourist destination.

Varadero → Freeport (Bahamas)

The Bahamas, once a haven for pirates, now thrives on tourism and maritime trade.

Pirates of the Lucayan Seas

Crossing open water, you enter the scattered islands of the Bahamas. These waters once belonged to the Lucayan people before European arrival changed everything.

In the 17th century, pirates ruled here—most famously Blackbeard—using the countless islands as hiding places. From above, the shallow turquoise banks appear peaceful, but they once concealed ships waiting to ambush Spanish treasure fleets.

Freeport → Santo Domingo (Dominican Republic)

Santo Domingo is the oldest European-established city in the Americas.

The First Colony

Approaching Santo Domingo, you arrive at the birthplace of European colonization in the New World. Founded in 1496, it became the center of Spanish power in the Caribbean.

Here, the story of conquest begins—indigenous populations devastated, and African slavery introduced. The Caribbean’s identity begins to take shape, forged in hardship and cultural fusion.

Santo Domingo → San Juan (Puerto Rico)

San Juan is a fortified city shaped by centuries of defense.

Walls Against the World

The coastline of San Juan rises with imposing stone forts like El Morro, built to defend against invasion. Spain fortified this island heavily, knowing its strategic importance.

From above, the geometry of defense is clear—thick walls, angled bastions, and a harbor protected at all costs. Yet despite these defenses, the Caribbean remained contested ground for centuries.

San Juan → Sint Maarten

A unique island divided between two nations.

An Island Divided

Landing at Princess Juliana International Airport, you arrive at one of the most iconic aviation locations in the world.

This island is split between French and Dutch control—a rare example of peaceful division in a region once defined by conflict. The Caribbean begins to shift here, from battleground to destination.

Sint Maarten → Saint Lucia

Saint Lucia is known for its dramatic volcanic peaks.

The Volcanic Crown

Flying south, the islands grow more rugged until the twin Pitons of Saint Lucia rise sharply from the sea.

These volcanic spires are remnants of the region’s violent geological origins. The Caribbean is not just shaped by history—but by fire beneath the earth itself.

Saint Lucia → Port of Spain (Trinidad & Tobago)

A cultural crossroads influenced by Africa, India, and Europe.

Rhythms of the Caribbean

Arriving in Port of Spain, the cultural depth of the Caribbean becomes unmistakable. Here, African, Indian, and European influences blend into music, cuisine, and tradition.

Carnival, steelpan music, and vibrant festivals reflect a region that transformed suffering into identity and celebration.

Port of Spain → Cartagena (Colombia)

Cartagena connects the Caribbean to mainland South America.

The Empire’s Stronghold

The walled city of Cartagena stands as one of Spain’s most important ports in the Americas. Gold and silver once passed through here, guarded by massive fortifications.

From pirates to imperial fleets, Cartagena represents the final chapter of Caribbean colonial dominance—where sea routes connected continents and shaped global history.

Final Reflection

The Caribbean is often seen as paradise—but beneath its beauty lies a story of exploration, conquest, resistance, and cultural rebirth.

From Havana’s revolutionary streets to Cartagena’s ancient walls, each island and coastline carries echoes of those who came before—indigenous peoples, colonizers, enslaved populations, and those who built new identities from the past.

Flying above it all, you witness not just islands—but a living narrative, scattered across the sea, forever shaped by wind, water, and time.