Immigration Vacation. Permit Purgatory. The Work Visa Waiting Game.

Whatever they call it on your rock, this hair-pulling, soul-sucking, confidence-crushing period stands between many of us Island Girls (or Want-to-be-Island-Girls) and our tropical residences of choice. Most of the idyllic Caribbean islands we sun-seeking sisters set our eyes on require you to secure a work permit or visa in order to live on your rock and hold gainful employment. Paperwork processes like these are stressful enough in the “real world” but when you sprinkle sand, sun, and island time into the bureaucratic mix, it can be downright agonizing.

I’ve had the privilege/pain of sitting through two such Immigration Vacations, comprised of that unknown period of time after you’ve submitted your paperwork when you are forced to wait for as long as it takes for a complete stranger in a tiny, stuffy office in some government building to decide your island fate. Whether you’re changing jobs, changing islands, or trying to make your first island move, this waiting game is the great equalizer. Unless you happen to have been born on your island of choice, no one is exempt from this process. Even the coolest cucumber can be reduced to a self-pitying puddle by the sheer unknown of this waiting game.



To make matters worse, in many cases you either can’t be working, can’t physically be on the island, or both while your permit is being processed. This means you may find yourself unemployed and/or homeless and/or lonely AF for an indeterminate amount of time. I am currently trying to grin and bear my way through an Immigration Vacation brought on by a move from my first island home, Grand Cayman, to what will hopefully be a new adventure on Virgin Gorda, BVI – assuming my permit goes through eventually…! I am lucky enough to be holed up at my parents’ house while I am in limbo, but I have friends who have had to couch-surf or have even been stranded at hotels they can’t afford in other countries while waiting for the big OK for weeks on end. And even though I am benefitting from a free place to stay, home-cooked meals, and am surrounded by loved ones, let me be if not the first then the most impassioned to tell you: THIS WAITING GAME IS ZERO FUN.

I set out five weeks ago to fully embrace this bonus visit with my family, the first time I’ve been home since I became an island girl and our fist visit together in about eight months. But… surprise surprise – living back at home is HARD. It is even harder when you have no idea how long you’ll be there. Honestly Mum, I’m 30 years old – I didn’t call you from Cayman every day to tell you I was home safe so WHY DO I HAVE TO CALL WHEN I’M LEAVING THE MALL NOW? Also, I‘ll see your regular long distance relationship pressures and raise you the added complication of sharing a bedroom wall with your parents. Seriously, I can hear my dad snoring through the wall. I can barely bring myself to say I love you out loud to my poor boyfriend for fear my mum can hear my whispered sweet nothings. He can definitely forget about any long distance hanky-panky or phone fun. No way, Jose (though his name is Andy, not Jose).

Furthermore, while this may not come as a shock to ladies as worldly and well traveled as you, but just a friendly reminder nonetheless: Canada can be REALLY FREAKING COLD! After two years away, I have successfully acclimated to my chosen Caribbean climate – anything under 20°C requires a sweater for me. My second night here, the temperature dropped to 9°C overnight. I haven’t seen single digits in years and it now requires double digit layers of clothing to cope. My fellow Canadians are prancing around in sundresses and short sleeves after a long and brutal winter. I was dressed like the Michelin man complete with a 90s puffer vest, wool socks, and a toque. In May. I am NOT cut out for this shit anymore. So while I planned to go for runs, eat healthy, and get fit while I waited for my permit, the *cold* reality is that most of the time, I’ve been huddled under multiple blankets getting annoyed with Netflix for asking me if I’m still here (check the temperature Netflix, I’m not going anywhere!).

Don’t even get me started on the anxiety, the self-doubt, and the stress-induced ulcers. Seriously, I’ve bitten my cuticles to the quick, the bags under my eyes get darker with every passing sleepless night, and my stomach has done enough flips to qualify for an Olympic tumbling routine. There is something about my island destiny being in the hands of some nameless, faceless government official that makes me feel unworthy of island life, unlikely to ever reach my island home and unbearably helpless. The tanned, happy-go-lucky island girl who left Cayman a few short weeks ago seems like a distant memory. I refresh my email at least a dozen times a day, holding my breath, and crossing my fingers for that golden ticket that will send me back to island life and love.



With all this uncertainty, it is easy to forget that being an island girl is as much a state of mind as it is a geographic location. Even off our islands, we are still the badass beauties who cure everything with coconut oil and choose to see the humour in island time and unpredictability. The calmer, happier, more centered version of ourselves that emerges on our rocks is also attainable in the “real world” – it may just take a little more rum to get there!

So while I snuggle under my heated blanket, pretending my Irish coffee is actually a daiquiri, and pressing the refresh button on my email one more time, I try to remember that I am pursuing the life that fills me up with sunshine, sea, and serenity. And I know I don’t have to tell you Island Girls that the wait will most definitely be worth it in the end.

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Did you have to endure an Immigration Vacation of your own before being able to settle on your rock of choice?

Written By:

Current Rock of Residence:

In limbo between Grand Cayman and Virgin Gorda, BVI`

Island Girl Since:


Originally Hails From:


A proud Canuck, Hali B has discovered she is best suited to a long distance relationship with her country of birth. After moving to Grand Cayman on a whim two years ago, she has truly embraced the roller coaster that is island living. This sun-worshipper has never once managed to wash all the sand off after the beach and has absolutely no idea what happened to her closed-toe shoes (nor does she care!). Her favourite island activities are lounging in the sun with a good book, scuba diving, beach walks with her beloved, and day dreaming of a time when she is grown up enough to care for an island puppy of her own. She is currently in the process of relocating to the BVIs in pursuit of more island adventures.

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