It seems like every couple of years, what feels like a mass exodus takes place. All of a sudden, friend after friend, acquaintance after acquaintance, is moving off island, most often headed back to “the real world.” Life on a rock is very transitory in nature, giving the impression that nearly everyone views their time here as a temporary interlude in their otherwise normal life path – one that always had an expiration date attached to it from the beginning. It’s currently one of those times again: lots of goodbye brunches and farewell cocktail parties, lots of people moving on.

In my early island years, I wanted to throw myself around people’s ankles, theatrically begging them to reconsider and stay, and couldn’t imagine what my life here would be like without them in it. Perhaps it’s because many of us are transplants and that this shared experience of island living is so different to what most of us are familiar with, but island life, much like the battlefields of love and war, cultivates deep friendships in impressively short periods of time.


Private jet plane is going to land at the airport of a tropical


Over the years, I’ve gotten better at goodbyes. At this point, I’m almost expecting people to leave before they even make the decision themselves and therefore, the inevitable news doesn’t come as much of a surprise anymore. Though as each person makes their grand exit, no matter how many times I’ve been through it before, it still always brings me pause to reflect on what it would be like to be the one on that plane, watching the islands and sea fade into the distance, knowing it would be a very long time until I’d see it again. It’s this scene that never fails to well up my eyes with tears and put a lump in my stomach, effectively telling me it’s definitely not my time for that yet, if ever.

Gratuitous emotional moment then pushed aside, I shift gears and turn my focus to the culture shock that surely awaits the departed back in society and have myself a conspiratory giggle. For whether you’ve been here for one year or five, after any significant period of your life spent on a rock, most everywhere else is a sharp contrast to everything you’ve inadvertently become accustomed to.

And so, as I write my goodbye notes, I thought I’d pen a cumulative one, to all the departing island peeps out there – past, present, and future.


Dearest Departing Friend,

It is such a bummer to see you go. You’ve become one of my favorite people to drink with, boat with, beach with, laugh with, and yes – bitch with. I can’t say I didn’t see this coming – in this last year I’ve watched your humor for the island wane and evolve into a bitterness I don’t quite share. I had secretly hoped it was just a severe case of Rock Fever, but as it turns out, you have fallen out of love with this place. And for that reason alone (my selfish wanting-you-to-stay desires temporarily quelled), I am trying to be happy for you that your wish to leave is finally coming true.

While it’s hard to keep the Survivor references out of our remaining conversations (“Outwit, Outplay, Outlast!”; “Quitter!!”; “You have been voted off the island. The tribe has spoken.”), I am doing my best to be supportive of your move. Quitter. Ok – sorry – that was the last one.



The tribe has spoken.


I know you’re looking forward to all of the abundance that awaits you in the Land of Convenience. But for my benefit, I’d like to request in advance that you control your urge to text me every time you so casually grab a Starbucks, or find 68 varieties of reasonably priced, perfectly ripe heirloom tomatoes at your local farmer’s market, or receive stellar (now normal) customer service. I get it. It’s going to be awesome.

As the one left behind so to speak, I’d rather you share with me your hapless missteps in failing to integrate back into civilization. Make me laugh. I need it. I’m missing you, Quitter.

Tell me about how you are having a miserable time following directions that use actual street names instead of landmarks and how much you miss the simplicity of just telling people to “turn left at the dumpster” to find your house.

Tell me how your toes are dying of Suffocation Disease from being forcibly contained to shoes everyday and how the soles of your feet have hardened without their weekly sand buffering treatment.

Tell me how you nearly got tackled for trying to carry your cocktail out of the bar and how what you miss most (besides me, obvi) is roadies.

Tell me how the first time you had to drive on the freeway again it was like that scene in Clueless, where you went into full-blown panic mode, screaming “The Freeeewaaaay!!” due to the overwhelming speed and activity of it all.



Tell me how aggravating it is to enter the bank, or the post office, or anywhere really, and not have every random stranger greet one another with “good morning/afternoon.” Seriously – rudeness.

Tell me how you took a hike and were more than slightly displeased that there wasn’t a bar at the end of it.

Tell me how cold you are all the time and how wearing bras everyday instead of just bikini tops is just as annoying as you thought it would be.

Anyway, I guess what I’m asking you to do is keep the sparkle to a minimum. I realize we’ve both made our choices – you, to go, me, to stay – and everything is a trade off and that there are perks to both of our homes. But still. I just lost you, the wound is still fresh, and I am not yet in an emotional position where I’m ready to re-mourn the loss of good Mexican food again. In exchange for you not rubbing all of your Plenty in my virtual face, I promise to do the same and keep the breathtaking sunset and boating pics to an absolute minimum, especially in December, January, and February.

But no matter your trials or triumphs as you readjust to your new big world, just remember that the islands will always be here waiting for you should you feel the need to escape and return to your barefoot days. That’s the best part – you’re now in on the secret that there’s another lifestyle option available to you. One that exists just south of normal – a funny, funky Bizarro World in the Sun that you know is not a dream, but an actual screensaver you can live in for as long as you can stay sane (or, until the rum runs dry). And, you have friends here.




The tropics stay in your blood forever – that is an irrefutable fact of science. Once an island girl, always an island girl.

Wishing you all the best on your next adventure,

Your Fellow Castaways Still Limin’ on de Rock

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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