I left the white, snowcapped mountains of the Canadian West Coast and migrated south to a Caribbean island. I traded altitude for sea level, black bears and squirrels for tropical birds and lizards. I left a heart at home and brought a soul on the road.

First Impressions

Like Whistler in BC, the beaches of Thailand, Sayulita in Mexico, or Goa in India, Grand Cayman is another bubble in the world. With few true locals (mostly of Jamaican and West Indian ancestry), the island feels largely shaped by expats — Canadians, Americans, and a few Brits. Many come for a season, a couple of years, or sometimes never leave. Sound familiar, Whistlerites? There’s something about this place that keeps people here. Maybe it’s the endless summer, the isolation, the party life, or simply a soul-searching journey. Whatever the reason, everyone seems to find their escape on this little piece of Zion.

The islanders are deeply religious. All bars and clubs close at midnight on Saturdays and Sundays, and on “Christ Day” almost nothing is open — not even public transport (a real pain if you’re trying to get to work).

Smoking feels like a national pastime (okay, maybe not 99% of the population, but it sure seems that way). Thankfully, the Cayman Tobacco Law of 2009 keeps public spaces smoke-free.

At first glance, the island looks clean. But look closer — there’s no recycling, no bottle depot, and the highest point here is Mt. Trashmore, the garbage dump. There’s a long way to go to catch up with the so-called “Western world.”

What I’ve Learned

Originally inhabited only by turtles, lizards, and caimanas (large marine crocodiles), the Cayman Islands were discovered by Christopher Columbus in 1503 when his ship drifted off course. For almost a century, the islands remained unsettled, but pirates and sailors stopped here to hunt turtles and lizards for food. Later came Europeans, refugees from the Spanish Inquisition, and deserters from the British army in Jamaica. By then, half the population were enslaved people.

In 1794, the “Wreck of the Ten Sails” changed the islands’ fate. After ships struck an East End reef, locals helped rescue most of the crews. King George III, grateful for their heroism, granted the Cayman Islands tax-free status.

Hotels and condos only started mushrooming along the shoreline in recent decades. With cruise ships docking daily and cheap flights from Miami and Atlanta, Grand Cayman became a playground for tourists. Seven Mile Beach brims with floating bars, banana boats, and day-drinkers chasing the sun.

A Day Off

After six straight days of 10-hour shifts, I finally had a day off. The girls and I scored a ride with a boat captain and headed to Stingray City. The morning sun was dazzling, the water hypnotic. I felt like a grain of sugar dropped in a Blue Curaçao cocktail. We claimed spots on the front trampoline of a 40-foot catamaran, Jack Johnson playing through the speakers, and set sail.

An hour later, we were standing waist-deep on a sandbar in the middle of the ocean, surrounded by wild stingrays. From tiny 20-pound males to 200-pound females, they glided effortlessly around us. At first, it was overwhelming to feel them brush against my legs — but once I relaxed, it was magical. Soft, curious, majestic. Definitely one for the list.

#63. Swim with the stingrays √

We sailed back with warm wind on our faces. Lunch was burgers at Lone Star (yes, I’m still fascinated by Canadian-sized portions), then frozen drinks at Rackham’s waterfront bar in Georgetown.

That afternoon, we went diving off the south shore. I was nervous — it had been since Sri Lanka, and I’d logged maybe seven dives in total. No instructor this time, just my Open Water card, rented gear, and friends. Luckily, Eva’s boyfriend was experienced and patient.

Once underwater, nerves gave way to awe. I felt like a tiny flea dropped into a bag of tropical Skittles — so many colors, so much life. I’d dove Panama and Sri Lanka, but this was beyond anything I’d seen. Fish, turtles, reef sharks, caves — everywhere I looked, something new. I felt free, weightless, at peace.

We surfaced to rain streaking the horizon and a brilliant sunset. Swimming back to shore, I thought: this is island life.

Work, Wine, and Wonders

Back at work, it’s constant chaos — but for once, I don’t mind. I have no dog waiting at home, no dinner to cook. All I can do is work, save money, and make the most of it. Still, I carve out little joys: a fruit sangria on Decker’s terrace, lunch at Calico’s beach bar, or late-night tapas at Agua’s Lounge (industry discount included). Their tuna tartare and beef carpaccio, paired with a crisp glass of wine, taste like a reward.

Yes, I feel homesick sometimes. It’s new to me — I’ve always travelled with someone before. But this is something I need to grow through. Slowly, I’m building connections here. And while my roots and my heart are still back home, I know these friendships and this experience will shape me. I’ll grow new leaves.