I arrived on the 4th of July. Like many islanders, I came searching for a new light — to shake up the mold, create new experiences, and start a chapter of my own.
This wasn’t a plan. It showed up as an opportunity, at just the right time — when my heart needed recovery and my soul was ready to hold on to something new.
I’d never thought much about the Caribbean before. To me it was touristy, full of big hotels and all the things I usually avoid when I travel. But this wasn’t about backpacking. It was about leaving home, on my own, at an older age, and stepping into the unknown. I had no expectations — just a work permit, a one-way ticket, and an open heart.
The first months were tough. I missed friends, my dogs, the family I’d built over nine years. I missed the mountains, the lifestyle, the fresh air of the Canadian West Coast. I missed home. But there were reasons I was here. I needed to push through the loneliness and give myself over to this island life. After two months in an old hotel room, I found a small condo on the beach. When my co-worker Jo from Whistler arrived, it felt like a piece of home had followed me here. That’s when life began to shift.
Fourteen months later, I sit on my balcony with a latte, looking out at the Caribbean Sea, remembering it all. The taxi dropping me off, the humidity instantly claiming my hair. My toes in the ocean, marking the Caribbean as mine. My first kiss with a stingray. My first dive into the clear waters of the Antilles. Wakeboarding at sunset, hold on tight, convinced I’d be shark bait if I fell. Jetskiing rough seas, clinging to life. The parties, the too-much Jäger, the nights I thought I’d forget but now hold onto. The friends who came, the ones who left, the ones who lit the way for future dreams.
I remember the pride of welcoming my mom and friends into my little paradise. Walking barefoot to beachside lunches. Watching sunsets on the way home from work. Snorkeling in my front yard. A quick weekend with my mom in Cuba. Diving at dawn and showing up to work with a mask mark across my forehead. Cheering with my roommate as we bought a Jeep with two months left on our lease, a Riesling bottle in hand. The DJs, the boat parties, the famous Sunday Fundays. Like steering a small vessel, I navigated my island life through it all — sometimes with a bottle in hand (no judgment, it’s island living).
It’s been a wild ride — a rollercoaster of challenges, joy, and memories I’ll carry forever. No regrets.
Cayman Islands, I raise my glass to you: thanks for the ride. Ya man!
Footloose Diary 