Chatter from down the beach wafts my way in the wind. And for just a moment, I imagine I am listening in on a casual talk amongst dogs.

“My owner arrives tomorrow.” 

“Ours just left. I’m exhausted. My liver needs a week off.” 

“What about you? When do your owners get in?”

*click for image creditBut no, this canine-esque conversation is actually a rather common one amongst the two-legged humans on the shore.

Since the majority of us in the islands tend to be employed in the hospitality industry, we all have owners. Whether it’s the owner of the restaurant we work at, the resort we manage, the villa we care for, the boat (or yacht) we work on, or even the actual island that we run. They are the rich and the uber rich and among the many things they own, they own us as well (at least in the figurative sense).

Though surprisingly enough, having as many billionaires floating around these waters as we do, there is a pleasant lack of snobbery, superiority, and the general obsession with status that tends to permeate upper crust circles in other parts of the world. The affluent who are attracted to the Caribbean, rather than somewhere decidedly more glamorous like Aspen or Monaco, are often drawn for the same reasons most of us decided to move here as well: the laid back vibes, the carefree fun, the low-maintenance lifestyle, and the privacy.

Down here, often times nobody knows – let alone cares – who you are or what you do/did back in the “real world”. People decide if they want to spend time with you or not based on your merits in the bar talk arena, rather than how many zeroes are in your bank account. In the states, the first question people always ask you is, What do you do?, and judge your worth accordingly. I imagine the notable decreased frequency with which this question comes up on a rock provides just as much, if not more, of a reprieve for the billionaires as it does for me.


For the Caribbean is the great equalizer. There’s something about the combination of sunshine, alcohol, and how the current can carry away the heaviest of burdens – at least for the time being – that seems to bring people back to the same level. Here, we’re reminded that we’re all just people. People who want to relax and enjoy life. People who like to get drunk and party sometimes like they did in college for a night (or two), free of guilt or criticism for being “irresponsible”. People who want to swim and nap and play and run around naked like they did when they were kids. People who want to escape the oppressive race that the world they live in holds them hostage to. People who like to talk to other people, just for the sake of relating and enjoying another human’s company, without the pressure of preconceived expectations.

It is here I get to occasionally cross paths with people who are literally shaping the world. Entrepreneurial giants, movie stars, musicians, legends of sport… people who back in the “real world”, I could never imagine meeting, let alone doing shots with. Yet here, it doesn’t hold the same weight as it would back there. Here, it’s so easy to forget about the things that make these people seem so utterly remote and unreachable elsewhere. Perhaps it’s the fact that we’re all barefoot. Or maybe it’s just that living down here, you’re so out of the loop with pop culture and have no idea what everyone is obsessed with until months after fads have already passed. Either way, it’s refreshing.

Typically, spending so much time within such close proximity to these levels of wealth would lead to a lot of envy, and even increased motivation to work harder towards the capitalist cause. But not in the Great Equalizer. The billionaires may own the islands and the toys on them, but we get to play with them too. And in spending time with these owners, I often get the inkling that a part of the reason they like to party with us is because on some level, they envy our lives – for we’re the ones who get to enjoy this all year round. We’re the ones “living the dream” that people from all walks of life fantasize about. As I sit on the beach of an island, watching its owner run around with a machete, barefoot and shirtless, tanned to a crisp, climbing coconut trees like one of the lost boys from NeverNeverLand, it’s clear that no one is immune to the Caribbean and its magical energy.

*click for image credit

Sure, we still get the occasional princess off a yacht who decides to come into the bar wearing head-to-toe Gucci, spike heels, and carrying a yippy dog in a sparkly bag. But rather than gaze at her with admiration and coveting her bling, here, everyone just shakes their heads and laughs as they watch her tottle across the dock, heels getting stuck between the planks. Didn’t she get the memo? We’re in the Caribbean. No one cares about having a Gucci unless it’s some kind of blended cocktail with rum in it.

Written By:

Current Rock of Residence:

Virgin Gorda, BVI

Island Girl Since:


Originally Hails From:


Chrissann’s home rock in the British Virgin Islands feels bigger to her than it actually is. Though after spending five years on a teensy one acre island, the current 13-mile long rock she’s residing on now IS ginormous, at least by comparison. As with everything in the tropics, it’s all about perspective.

Once upon a time she used to care about things like matching her purse to her pumps but these days, any activities that require a bra and shoes go under careful, is-this-even-worth-it consideration. If island life has taught her anything at all, it’s that few things are more rewarding than time spent in the pool with a cocktail in hand.

As the Editor in Chief of this site, she spends her days working from home with her blue-eyed sidekick, Island Dog Diego, writing, editing, and cultivating content in the hopes of bringing some laughter and lightness to her fellow island souls. She recently published her first children’s book, When You’re a Baby Who Lives on a Rock, and is pretty pumped to share it with all of the island mamas out there. Her days off are typically spent boating, hiking, and meeting up with the neighborhood’s imperious roadside goats, who she shamelessly bribes into friendship. While normalcy was never listed as one of her special skills, Caribbean life may indeed be responsible for new levels of madness. She attributes at least a smidge of her insanity to the amount of time she spends talking to drunk people.

If you’re somehow still reading this and feel inclined to find out more about this “Chrissann” of which we speak, you can also take a gander at her eponymous website or follow her daily escapades on Instagram @womanonarock.

Want to read more posts by this writer? Click here.

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