Nestled in the western Caribbean Sea, the Cayman Islands are a trio of tropical jewels—Grand Cayman, Cayman Brac, and Little Cayman—each kissed by turquoise waters and ringed with coral reefs. From Chicago, it’s a breezy 4-hour flight southward, a journey that feels like slipping through a portal from bustle to bliss. Grand Cayman, the largest of the three, spans just 76 square miles—small enough to explore in a few days, yet vast in its offerings of wonder.
The islands first entered European consciousness when Christopher Columbus sighted them in 1503, naming them Las Tortugas for the sea turtles that crowded their shores. Later, they became entwined with Jamaica’s colonial narrative, sharing governance under British rule. Today, they remain a British Overseas Territory, with Queen Elizabeth II’s legacy still visible in the architecture and institutions. The Indian diaspora—drawn here through trade, hospitality, and entrepreneurship—adds another vibrant thread to this tapestry, echoing the global currents that shaped the Caribbean.
Perched on the iconic Seven Mile Beach, The Westin Grand Cayman is more than a resort—it’s a sanctuary. Morning light spills across powdery sands, and the sea hums a lullaby just steps from your room. The infinity pool glistens like a mirror to the sky, while the Hibiscus Spa offers rejuvenation steeped in island botanicals. Dining here is a sensory celebration—grilled plantains, coconut curry, and mango-infused salads served with ocean views that stretch into eternity.
The Cayman Islands pulse with the rhythm of its people—Jamaicans, Indians, Caymanians—all English-speaking, all welcoming with a smile that feels like home. Having spent middle school in Jamaica, I felt an instant kinship with the island’s cadence. The food reflects this cultural blend: jerk-spiced tofu with roti, callaloo sautéed in coconut oil, and samosas filled with island-grown vegetables. It’s a culinary conversation between continents, served with coconut rice and laughter.
A boat ride out to the reef reveals a kaleidoscope of coral gardens and darting fish—parrotfish, angelfish, and the elusive barracuda. Then comes the surreal encounter at Stingray City, where gentle rays glide around you like silk shadows. These creatures, once feared, now invite awe and respect.
A short hop away lies Starfish Point, where crimson and gold starfish dot the shallows. But a gentle reminder: admire them in the water—lifting them out can harm their delicate systems.
Ask for Captain Chris and his boat tour at your hotel concierge. He and his team are the best, most fun and not just take you to the spots, but teach you along the way. (Phone: +1 345-322-8011)
Every summer, the streets of George Town erupt in color, music, and movement during CayMAS Carnival. It’s part of a broader Caribbean tradition—an exuberant celebration of freedom, identity, and rhythm. Feathers, sequins, and soca beats swirl through the air as locals and visitors dance in unity. It’s not just a party—it’s a living story of resilience and joy. If you happen to be there in July, make sure to step out of your room and into the streets and if you put your inhibitions away, dance away.
The Cayman Islands offer more than just a vacation—they offer renewal. Whether you’re floating in the shallows, sipping fresh coconut water beneath a sunset, or tracing the footprints of history, this place invites you to pause, breathe, and belong. For anyone seeking rest, reflection, and radiant beauty, the Caymans are calling.
Karthik Raja 