Category: Caribbean

Several times in my younger years, I wondered how life might have been if my parents were rich: annual holidays to Florida, Mexico, or Barbados, or maybe Dad landing a big promotion and moving us to Atlanta, Hawaii, or even Japan. I pictured starting fresh — a new school, new friends, new streets, new routines. It was the kind of adventure I longed for. Even as a kid, my soul was restless. Daydreaming was my specialty. Science and math weren’t my strong suits, but writing and storytelling came easily. In my imagination, Falkor would stretch a paw through the classroom window and invite me to fly away.

I dreamed of things I didn’t have: a house full of siblings, parents together, walls lined with family portraits, yearly sun-drenched vacations. Instead, it was me, my single mom, my brother (off traveling the world), a wild orange cat, and a pack of dogs. And honestly, I wasn’t unhappy. My mom worked hard, loved harder, and taught me values more precious than money. I didn’t have a dad, but I had her — and that was enough. Still, watching American TV shows filled with big families, palm trees, and shiny universities, I couldn’t help but wonder: could I taste just a little of that life?

When I moved to Whistler in 2003, I left everything behind to face the unknown. No plan, no clear idea of what was next — just a backpack and the restless heart of a 19-year-old. I started out scrubbing toilets and serving spoiled guests. Then came a break: a job at one of the best patios in town, the very one that had caught my eye on my first day dropping off résumés. My English was rough, so at first customer service seemed out of reach, but persistence paid off. I went from sharing a garage with a stranger to living in a luxury condo on the mountain: a master bedroom, king-size bed, private fireplace, and a patio with a view of snowy peaks. For a while, I lived like a princess.

A couple of years later, I moved into a big house with my boyfriend, his brother, his girlfriend, and close friends. Three fireplaces, a pool table, a movie room, a sprawling backyard, and a chef’s kitchen — a $1.3-million home. We shared meals, laughter, fights, tears, and endless conversations about life. We were family. For the first time, one of my childhood daydreams had come true.

But even in Whistler, with everything I thought I wanted, it wasn’t enough. I traveled across the country, worked, built a life. At 26, I had a good job, a boyfriend I loved, a dog I adored, amazing friends, and a life full of adventures: sledding, boating, camping, fishing. On paper, it was perfect. Inside, something was missing. One day, my boyfriend said: “Capu, you’re not happy. You need a new experience.” As hard as it was to hear, he was right. I couldn’t stay still.

So I packed my bags — nine years of life left behind — and leapt into something new.

Back in Whistler, I used to dream of palm trees, a Jeep, a bungalow by the beach, and friends flying in to visit. And here I am now. At first it was just a moldy hotel room at Treasure Island, but eventually I found a condo by the sea. Now I wake to the sound of waves, sip my latte on the balcony with the Caribbean stretching out before me, and think: Wow. Life is good. With persistence and determination, I got what I wanted. Again.

37. Live and work overseas √

Update: I did get the roofless Jeep. And yes — my friends, and my mom, came to visit.

8 weeks. 10 bottles of wine. 37 takeouts. 20 extra pounds. And more island highballs than I can count.

Nights of too many Jägerbombs, waking up with cereal in my hair. Ridiculous nights at O’Bar, nO’Bar, where’s-my-hO’me Bar. Messy room, moldy clothes, a view of the parking lot. That was it. I was over it. I didn’t come here to rewind ten years and live like a teenager. I’m 27 now, and it’s time to focus on why I came here in the first place. Time to grow up, honey.

Don’t get me wrong — I had fun. It felt like college all over again: flying free with no one telling me what to do, no one to boss me around. No obligations, no responsibilities beyond showing up for work and paying rent on time.

Work, sleep, eat, drink, repeat. No wonder I gained those 20 extra pounds. In the service industry, late nights come with the territory. A drink after work to cool down, then after six days straight on the job, that one fabulous day off — and its thirst. A chance to let loose, make memories, and put new stories on the wall. And as someone trying to make friends, what better way than to spend money and time on food and wine? (Okay, maybe too much wine. Do I drink too much?)

But here’s the thing: I didn’t come here to party my life away. I came to grow, to learn, to finally do things on my own. I have a list of goals, and I can’t leave this island without checking them off.

So hello, September — bring on your wisdom. Two months of “adaptation” was more than enough. After surviving a moldy AC room that gave me a nasty cough, I finally found the perfect condo by the beach. Call it luck, but really it’s the fruit of determination and hard work. I got what I wanted, again.

And timing couldn’t be better: Jo, my ex-coworker from Whistler, arrives this month to share this beautiful two-bedroom, two-bathroom unit. Now I’ll stock the fridge with fresh food and start cooking again. I’ll read the news in the morning on the beach with a familiar face. Sip Pinot Grigio after work on the balcony, watching the moon rise over the sea. Go to yoga at the studio next door. Swim in the mornings in my backyard ocean. Study my Advanced Open Water manual with a frozen margarita at the swim-up bar. Ya man.

It’s taken time to adjust — to decide whether I wanted to make this place my own. Different crowd, different air, different vibe. But now that I’ve left those rookie days behind, expanded my circle, and started leaning into healthier habits for body and mind, I look around and think… hey, island life for a while? Why not.

While I was devouring a piece of sushi with one hand and sipping a glass of Chardonnay with the other, a Puerto Rican tourist approached me at the tapas bar of Karma Restaurant and Lounge.

Tourist: So, I ask everyone I meet out of curiosity — where are you from, and what brings you to the Cayman Islands?

Me: I’m from Canada. I came here on a work permit and I wait tables at a local restaurant.

Tourist: Why did you choose to come here?

Me: The job offer was attractive and unique. And honestly, I needed a change — a new experience.

Tourist: What do you do back home?

Me: I work in the service industry at a ski resort. I’m basically a snowboard bum.

Tourist: Is Cayman your first trip outside of Canada?

Me: No, it’s actually my 15th country.

Tourist: Impressive! Where else have you been?

Me: I’ve road-tripped the American West Coast, drank tequila in Mexico, scuba dived in Panama, surfed in Costa Rica, camped in Hawaii, vacationed in the Dominican Republic, toured France and London, backpacked Thailand and Laos, tramped through India, trekked Nepal, visited the Dalai Lama’s home in Tibet, and holidayed in Sri Lanka. Now I’m here in Cayman for a five-month work holiday.

Tourist: Wow! You’ve been everywhere!

Me: Not even close. I’ve only been to 15 countries. There are about 196 in the world (197 if you count Tibet, which I hold close to my heart). So I still have a long way to go.

Tourist: You’re such a lucky girl.

Me: No, Sir. It’s not luck. I chose this path. Like everyone else, I have hard times and good times. I’m lucky to be healthy and to have amazing people around me, but the rest is just decisions I’ve made. Choices.

Tourist: Your parents must be wealthy if you travel this much.

Me: No. I only have my mom, and she does the best she can. All my travels are the result of my own work. I work in the food and beverage industry — it pays well, offers flexibility, and I can use my skills anywhere in the world. I know I don’t have a pension or financial security, but this is the risk I take to chase my dream of exploring the world. Or maybe just of conquering my own world.

Tourist: You’re right… I’m a technician. I only get two weeks’ vacation a year, so I don’t go far — that’s why I come here. I make good money and I’m saving for retirement. I have a wife and kids I love, a nice house, a car. But that’s it. This is my life. I have small memories, short stories. I live a routine. I work and work so that maybe, when I’m 60, I’ll be able to live my life.

Me: Well, Sir, having a family is a beautiful thing. And owning a home is comforting. Traveling the world is scary, and it’s not for everyone. But sometimes, you need to let go, listen to your heart, and do something crazy. Money shouldn’t be what stops your dreams. Make a bucket list and start checking it off. Live your life now. The future will always be there, but this moment will soon be gone.

There was a pause. He sipped his rum on the rocks, looked up, took a deep breath. Then, as he stood to leave, he said:

Tourist: Well, young lady, thank you for this beautiful conversation. If you’ll excuse me, I have a bucket list to start writing.

When I turned 19 and graduated from college, I left behind a boyfriend and friends, packed a bag, and set off down the unknown roads of life. I wanted new experiences, new friends, new challenges. I was staring at a blank page, ready to fill it with stories and memories. With no one to hold my hand across the streets of my destiny, I did it all on my own — and I’m proud of that. I built a life for myself.

Eight years later, I felt the urge for change again. An escape. When everything looked perfect on the surface, I still needed to leave — to go to a remote island, hoping that somehow everything would be okay.

Yes, it’s hard. Don’t get me wrong, I’ve met kind people and kept myself busy. I work a lot, make good money, spend breaks at the beach. But the long hours we all put in mean there’s little time to plan anything together. Days off never match. What I crave are activities that challenge me, body and mind — adventures, real conversations, something more than the four walls of work or the bottom of a wine glass.

Going out alone as “the new girl” can be overwhelming. It feels like the first day of school, with cliques already formed. I realize how long I lived in my mountain cocoon, safe and comfortable, shielded from contrast or conflict. At home, I could choose who to let in — and I was never alone. I miss that. I miss friends who became family, the hugs, the talks, the years of relationships that turned into gold. Without them, I feel vulnerable. Exposed.

This whole experience is scary, and I haven’t fully adapted yet. Some days I think about going home — to the people who love me, who understand me, who see me for who I am.

But here’s what I know: you can’t run forever. Not from your fears, not from your problems, not from home. Yes, I ran. And no, I don’t regret it. Because being here forces me to stay focused, to stay positive. I needed this. Not just to “have the experience,” but to truly face it, hold it, and make the most of it.

I have an itch I can’t quite scratch. I need to understand it, learn from it. I don’t know how long it will last — but I do know it won’t last forever. Because nothing ever does.

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.

July 4, 2011.
29ºC, feels like 41. Partly sunny. 11:54 a.m. (Eastern Time Zone, UTC/GMT -5).

Welcome to Grand Cayman Island!

I stepped off the plane and into the heavy heat. The sweater I wore to fight off airport air conditioning was useless now. Standing in line at immigration, surrounded by tourists eager for a week of sun, I felt out of place — just me, my photocopied work permit, and two suitcases, tangled up in nerves and excitement.

This was the moment to grow up. No chaperone, no companion, no mentor. Just me, in a foreign country, with no one waiting on the other side. Time to face reality, trust my instincts, and stay positive. Yes, I felt lonely. But I also knew this was my chance to push myself, to break out of the coconut shell I’d been living in.

After searching the airport for a currency exchange (and realizing there wasn’t one), I was glad I’d brought U.S. dollars. Tip: if you’re coming from Canada, exchange before you leave. You can use U.S. dollars here, but the exchange rate in shops and restaurants is much worse.

Next step: a taxi. The prepaid stand quoted US$20 for a 10-minute ride to Treasure Island. Pricey. Luckily, the woman behind me was headed the same way and offered to split the fare. Another tip: if you split a cab, let the prepaid stand know, otherwise you risk being double-charged. We weren’t, and had a lively debate with our driver before settling on the original fare.

I’d booked a room at Treasure Island Resort for my first month. At CI$1,000/month (about CAD$1,200), it was steep for my wallet but reasonable by island standards. The perks: a gym, two pools, a beach bar, and private beach access. The room itself was fine — double bed, sofa bed, kitchenette, bathroom, cable TV, and a phone. The balcony faced the parking lot, so the curtains stayed closed, but at least I was on the second floor, which felt safer during hurricane season. All in all, a decent starter pad.

After a shower, I left my bags unpacked, grabbed a map, and walked north along the main road. Subway, pharmacy, fruit bar, coffee shop, grocery store, liquor shop — all within reach. Forty-five minutes and two miles later, I reached my new workplace. Perfect timing: the staff were in a meeting about a new menu. I listened in, had a glass of wine at the bar, chatted with my new coworkers, then headed back “home.” Work would start tomorrow at 4.

A Week Goes By…

The restaurants I’d be working for — Eats Café, Legendz Bar, and Yoshi Sushi — were owned by a Canadian couple. Eats is a busy diner with eclectic décor, Legendz a sports bar packed with tourists and regulars, and Yoshi, of course, serves sushi. The kitchens are shared between them, just like the last place I worked in Whistler. I was assigned to Legendz.

Work was non-stop. With the Westin right across the street and loyal regulars, we were constantly busy. Six days a week, nine to ten hours a day, often in split shifts. So this was the Caribbean work ethic — exhausting, but part of the deal. In one week, I’d barely seen the ocean, my fridge was still empty, and my bags remained unpacked. But I was meeting good people, making contacts, and picking up tips on island life.

Walking those two miles in the heat every day wasn’t sustainable, so I started using the bus. At CI$2 a ride, it’s pricey for the short distance, and the system is unpredictable. They’re private minivans — you wave, they honk, they stop. After 9 or 10 p.m., though, they stop running. Which leaves me walking (not recommended with the rise in crime), overpaying for a cab, or relying on coworkers for a lift. Thankfully, people have been generous, even if most live north and I live south.

Tomorrow will be my first real day off. Kendra, a coworker, and I are planning to swim with the stingrays. It’ll be good to explore more of the island — so far I’ve only seen the stretch between work and home.

It’s only been a week. The first days were hard — I missed my friends, my dog, my life back home. Loneliness is still there, but slowly I’m finding my way.

I’ve had my share of trips and adventures, but this one feels different. I’m pressing pause on my life in Whistler and heading to the Caribbean for five months of work — this time, completely on my own.

YVR → SEA → ATL → GCM

I feel lonely. Not just because I’ll be alone, but because I’m leaving behind the friends, the life, and the dog I love to start over overseas. The challenge is real, and I can already feel the weight of it.

I already feel lonely. Not just because I’ll be by myself, but because I’m leaving behind my friends, my dog, and the life I built over the last eight years. That part is hard.

Grand Cayman isn’t a scary place — it’s safe, modern, and full of other expats. I’m not worried about the island. What I’m worried about is how it feels to start over from scratch, with no one waiting for me. But this is what I asked for: a challenge.

I want to see if I can do this on my own. Learn more about myself. Get stronger. It’s scary, but it’s worth trying.

So here I go. Chin up. I got this!