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Terrace in Negril, Jamaica.Cristian Lazzari/Getty Images/iStockphoto

Sometimes things don't go as planned, and those moments often make for the best stories. Tripping columns offer readers a chance to share their wild adventures.

On Sunday I popped the question: "Wanna get away for a week?" Last minute, whimsically. I suggested Jamaica. "I always wanted to go there, Negril in particular."

In my youth I worked in Grenada for a year, was married for 17 years to a rasta-without-dreads, and fell in love with roots reggae. But I had to persuade my Czech-man from Prague, son-of-a-refined-scientist, schooled lover of classical, opera, authentic rock and serious jazz. On Monday, he said yes. Friday, we took off.

Travel tests people. What turbulence can you transcend: A new five-kilogram carry-on limit dutifully enforced by the airline? A waitress who yawns while taking your order? Tepid water when bones chilled from hours in the sea yearn to be warmed by a hot shower? Four days in a row? Such travails. And nothing like we've just been through at home, post prostate cancer, and now a fresh cancer-free start.

After a supersmooth check-in to a fabulous ocean-front suite, we meet another test. Our room is in the resort's nudist section. We did not know this was even a thing. And it is not our thing. The website and TripAdvisor gave no clue.

"Busted," we confess to Kevon, our young host. "Yes, we are prudes."

"Ah, no problem mon. You'll love it. Everyone on this side is so friendly, you'll see."

Yes, that's the unfortunate point. We offer awkward objections. "No, really, you'll get accustomed."

We try. Open the French doors, step out on the balcony to take in the sea air and ocean spray. The colours are fabulous, and then, well-clothed, we greet a thong-less gathering of corpulent men sprawled "belly-scratch-doglike" in lounge chairs dotting the grounds in front of our suite.

We send Kevon away and converse. I love the room, the ocean view, the ease of check-in. I don't feel like fighting with guest services. I'm ashamed and self-conscious of my judgment, but I'm very aware of my fiancé's discomfort.

Still, I venture without conviction to salvage things. "Look. Here, I can sit on our lovely couch looking out at the ocean without interference from … Ooh, my. Oh, no …" Two portly elders rise, their opulence dangling in full reggae-lia.

I volunteer to call guest services. To our surprise and relief, they easily promise a room change, beach-front, in the clothed section.

It's wonderful, right by the ocean.

We begin to soak up what we came for; in the shade of the cottonwood, in the shadow of the full moon, in the warm light of the sun, in the caress of the turquoise waves. We walk and swim along the beach and move with the mellow pace of life.

"Do you know Cottage in Negril?" I ask the Rasta musician who's stopped to entertain for tips. It's the song that called me here so many years ago.

He sings it perfectly, in a sweet and raspy welcome home. It sparks the memory of One Love, and washes away our vacation's fleshy start. We've left the shades of grey behind in Ottawa for now.

Send in your wild story from the road to travel@globeandmail.com.

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