Some blogger friends recently celebrated the passing of their first 6 months on their island. Musing over their adventure thus far, they shared some of their “Notes to Self” to reflect on the lessons they have learned. As I read through their list, nodding all the way (yup, yup, yup – I remember that! ), it got me thinking about all the things I’ve learned over my 10+ years rockside.

The eccentricities of island life are good at weeding out the weak in spirit. Over the years, I have witnessed countless dreamers move down with a nothing but a suitcase and a smile only to run back to where they came from, tail between their legs, disenchanted within the first few months. Yes, there will be many days you spend watching a majestic sunset over the water, shaking your head, wondering how you ended up so fortunate. But there are also plenty of days that you will spend in a puddle of hot, angry tears, shaking your fists, wondering why the hell you stay here and deal with this shit. Sometimes the island is kind to you and bequeaths you with sunshine and rainbows and kittens; other times… not so much.


the baths virgin gorda


This post goes out to all the times the island has kicked me in the knees and pointed and laughed as I fell off the cliff. In retrospect, these lessons now hold tremendous comedic value for me – stories I tell often to remind myself how fucking resilient I have become – but at the time of the lesson learning, let’s just say there was less laughing and much more curiously strong cocktail imbibing taking place to suppress the fury.




Trying to reason with a police officer who has already decided to unjustly tow your car (and is likely getting a kick-back from the tow company as a direct result of this choice) is a waste of breath. Yelling and having a tantrum about the ridiculousness of it all when you don’t get your way will still get you towed, cost you much more money, and likely land you in jail.



Island tarantulas (also known as “donkey spiders” in some circles) reserve the right to bear arms. If you intend on killing one of these diabolical creatures, you better come in with guns blazing. They will not succumb to being smushed with one phonebook (two, either, it should be noted), being chased by a broom, or even with an electric mosquito racket. Be prepared to do battle. They will come back at you hard – a hairy, creepy fisticuffs you have not trained for. And when you lose sight of the monster when you inevitably run and scream in the other direction, resign yourself to the fact that you will be fitfully sleeping with one eye open for the next month, insisting you “feel something” on your body in 5 minute panicked intervals.


SPIDER scary meme



Opting to take your own open-top boat to one of the few fancy (ok, fancy-ish) island parties of the year (that you look oh-so forward to, as opportunities to dress-up are rare) will likely deliver you to said party looking like a drowned sewer rat. Plan ahead, leave earlier, and take the damn ferry. In the islands, rain will always happen exactly when you’re not counting on it to happen. You can bet on that.



Always carry a stick of deodorant in your purse. It is hot here. You will sweat. And you will end up stinking in the most inopportune of circumstances if you don’t plan accordingly.



When putting money into your Caribbean bank account, do not expect to have access to all of these funds at the same time. Pretty much ever. Much of it will bear the ambiguously intolerable label of “unavailable” during unpredictable time periods. Thinking this money belongs to you is a relic of your outdated stateside thinking. Do not rely on this bank account when traveling. Belgian hotels expect you to pay in full at check-out and there is no real way of explaining in a language you do not speak, using hand signals alone, that your Caribbean bank is a nonsensical bully who likes to punish you for your foolish decision to trust it.




Never go into a restaurant desperately craving anything. They are likely out of it. If they’re not and by some twist of fate you are actually allowed to order the menu item of your desires, do not get your hopes up yet. There is still a highly plausible chance that the server will bring out everyone else in your party’s food and only then turn to you to inform you they are out of your selection and tell you to order something else. Until your food is actually in front of your face, set before you at your place at the table, do not – I repeat, DO NOT – crave anything.



“Playing hooky” from your job is a reckless game here in Mayberry. Everyone knows everyone and unless you’re planning on staying locked in your bedroom with the curtains drawn, your employer WILL find out. If you call in sick, citing a severe case of The Pink Eye and you decide to go out boating anyway, you best be prepared to pour tequila directly onto your eyeballs to ensure they bear the fire of the devil as it is a near absolute certainty that you will run into your boss at the fuel dock. Or your boss’ wife.



Place all of your dry goods in fully-sealed ziplock bags/Tupperware immediately after you return home from the grocery store. Do not skip this step even if you did the “island flour check” (opened it at the market before you purchased it). Failing to do so can lead to a weevil infestation of epic proportions in your kitchen that will linger for months. Unable to fully rid yourself of these pervasive beetles, you will slowly but steadily go mad. Your insanity will culminate in a final mental breakdown of institutionalized proportions as you pour a box of what you think to be rice into your pan and end up sautéing yourself a dinner of weevils instead. Puking will ensue.




When apartment hunting, if the landlord seems slightly nutty initially, do not attribute this to a lovable quirk you will grow to cherish in a sitcom-y sort of way. Just walk away. It doesn’t matter how great the view is or what a steal of a deal the rent it, it is never worth it. Your island landlord is the almighty arbiter who decides if your stint in his/her villa is paradise on Earth or a living hell. Never forget that this is the wild west. Tenants’ rights you thought you had may very well not apply here. The levels of crazy that can be unleashed upon you for seemingly no reason at all by your landlord, aka the Thief of Joy, will astound you.



Leaving a pair of sand-crusted sneakers under your desk will plague your office with sand fleas who will attack your legs with such ferocity that you will end up scratching off your top layer of skin, unable to stop itching yourself like a deranged monkey. The only solace you will find is in the arms of a pricey doctor’s visit and some high-potency steroid cream. Though the itching may subside, the hateful red rash covering your body will cause people to look at your legs with a face of unspeakable horror that’s usually reserved for movies with the word “saw” in it. Your fellow humans will conspicuously avoid you for fear of contracting your “disease.”

– – –

What lessons has the island sucker punched you with and taught you the hard way?

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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