Island Hopping with Oliver: A Tropical Sailing Diary

There’s something primal, almost poetic, about sailing. The wind becomes your compass, the sea your road, and the horizon your promise. For Oliver and me, island hopping through the tropics was never about checking destinations off a list—it was about the rhythm of the waves, the curve of unknown shores, and the quiet satisfaction of chasing sunsets with no arrival time. This is our story—part travel diary, part soul-searching voyage—of two friends and one dream, unrolling like a nautical chart across a tropical paradise.

Day 1: Departure from Grenada

Grenada—known as the Spice Island—is where our story begins. The marina was busy that morning, with the scent of salt and diesel hanging in the humid air. Our vessel, Sea Wind, a modest 38-foot sloop with a cheerful yellow hull and teak trimmings, was more than a boat—it was home for the coming month.

Oliver, ever the practical one, was already coiling lines and checking charts. I, more inclined toward daydreaming, stood at the helm imagining turquoise lagoons and coral reefs. We'd planned this trip for over a year, but it still felt surreal.

As we eased out of St. George’s Harbor, the sea opened up like a welcome mat. The sails billowed, and the island faded behind us. Ahead lay a scattering of jewels: Carriacou, Union Island, Bequia, Mustique, and beyond. Our island-hopping adventure had begun.

Day 3: Carriacou – The Island of Reefs and Rhum

Two days in, we reached Carriacou, the smaller sister of Grenada. It's an island that feels like a whisper—quiet, warm, and slow in the best possible way.

We anchored in Tyrell Bay, where the water was so clear that even at 20 feet deep, we could see the shadow of Sea Wind on the sandy floor. Oliver and I snorkeled along the reefs off Sandy Island, marveling at brain corals and curious parrotfish.

That evening, we sipped locally distilled rum at a beach shack run by a man named Theo. He had sailed here from Martinique thirty years ago and never left. I asked why. He said, “Some people find paradise, and some people become it.”

We slept under the stars that night, rocked gently by the sea, the moon slicing silver light across the water.

Day 5: Union Island – Life Under the Volcano

Union Island rose ahead like a dragon’s back, jagged and lush. Clifton Harbor was lively—colorful boats, reggae music, and French creole mingling with English. The island's vibe was electric, a contrast to sleepy Carriacou.

We spent the morning at the open-air market gathering fresh fruit—papaya, starfruit, and limes. A local boy named Ansel sold us sugarcane and offered to guide us up Mount Taboi, Union’s volcanic peak.

The hike was sweaty and steep, but the view from the summit was unreal—an endless panorama of the Grenadines dotted like emeralds in sapphire.

Oliver stood beside me, quiet as always. “This,” he said finally, “is worth everything.”

I knew what he meant. The early mornings, the briny boat smell, the occasional seasickness—they all disappeared in the presence of something so breathtakingly raw.

Day 8: Tobago Cays – Turtles and Time Stopping Still

Nothing could have prepared us for Tobago Cays. Protected as a marine park, this cluster of tiny islets is surrounded by vibrant reefs and ringed by the palest blue water I’ve ever seen.

We dropped anchor near Baradal Island and dove into the sea. Within minutes, we were swimming with green turtles, graceful and unbothered. They grazed on seagrass as if we didn’t exist.

We kayaked to Petit Tabac—the same uninhabited island where parts of Pirates of the Caribbean were filmed. It felt cinematic in every way: palm trees bowed to the wind, waves crashed lazily on white sand, and there was not a soul in sight.

We lit a small bonfire that evening, grilled mahi-mahi on a makeshift grate, and watched the stars appear one by one. Island hopping wasn’t just a trip anymore. It was a trance, a dance with nature and time.

Day 11: Bequia – Pirates, Shipwrights, and Secret Bays

Bequia was the island I had read most about, known for its history of whalers, shipbuilders, and pirates. The main town, Port Elizabeth, nestled into Admiralty Bay, felt like a Hemingway novel brought to life.

We docked at the Belmont Walkway, a charming waterfront path dotted with cafes and galleries. Over a strong coffee and coconut tart, we met Jeanette, a Scottish woman who had been living on Bequia since the ’80s. “Bequia,” she said, “pulls at your bones. You think you’re visiting. But really, it’s adopting you.”

That afternoon, Oliver and I sailed around to Moonhole, a bizarre and beautiful eco-community built into volcanic rock. With no electricity and houses made from stone and sea glass, it felt like an elvish hideout.

We spent the night anchored off Friendship Bay, the boat cradled in calm water. There’s a stillness in Bequia that presses gently on your soul and tells you to slow down.

Day 14: Mustique – Glamour and Ghosts

We debated skipping Mustique, the jet-setter’s hideaway, fearing it would feel too polished. But curiosity won.

From the moment we docked, it was clear this was a different world. Opulent villas peeked from the hills, and the famed Basil’s Bar served $25 cocktails with names like “Mustique Muse.”

Yet beyond the glamour, we found something unexpected. At the island’s northern tip was Macaroni Beach, deserted and dramatic. We wandered for hours, collecting shells and swimming in surf that felt like silk.

That night, we drank rum quietly on the deck of Sea Wind. Oliver spoke of things he rarely did—his regrets, his dreams, the people he missed.

“There’s something about the sea,” he said, “that loosens the knots inside.”

Mustique wasn’t just for royalty and rock stars. It had its own ghosts, and maybe we were becoming part of them.

Day 18: Canouan and the Return Drift

By the time we reached Canouan, we were sunburned, salt-stained, and utterly at peace. The island was undergoing development—luxury resorts replacing old fishing huts—but the people still smiled the same, still waved from porches, still offered mangoes without asking.

We anchored in Grand Bay and simply rested. The days blurred—diving, sailing, laughing, sometimes saying nothing for hours. The kind of silence only great friendships can hold.

We knew we’d have to turn back soon. We checked weather windows, adjusted sails, planned our return. But it all felt background. The real voyage was inside us now.

Final Days: Homeward Bound, Changed Forever

Returning south through the Grenadines, retracing our path, everything looked different. Not because it had changed—but because we had. Island hopping wasn’t about places. It was about perspectives.

We saw Carriacou’s reefs again and noticed things we’d missed. Union Island’s volcano looked less daunting, more inviting. Even Grenada, as we approached the final port, shimmered with a kind of secret we hadn’t noticed before.

When we docked, I looked at Oliver. “Same boat,” I said, “but different sailors.”

He nodded. “The sea does that.”

Epilogue: What the Islands Gave Us

Island hopping with Oliver wasn’t just a sailing trip. It was an awakening.

We learned the art of slowing down. We tasted the rhythm of the sea. We discovered that islands are not isolated dots on a map but stories waiting to be heard—each with its own soul, its own scent, its own siren song.

But most of all, we found clarity in motion. The boat rocked, the islands shifted, and through it all, we became lighter versions of ourselves.

And maybe that’s what all great journeys do. They return you to where you started, only now you’re carrying treasure—not gold, but memory. Not maps, but meaning.

Would we do it again?

In a heartbeat. Or perhaps…in a wind gust.