So much of the comedy of island life lies in its ironic nature. Few things go as planned around these parts. In fact, a surefire way for something not to go as expected is to set expectations in the first place.

We women on the rocks got our brains together for a fun little collaborative post. Here are some of our favorite examples of island irony at its finest on our various islands…

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“By law, you have to wear a seatbelt in St. Thomas and the police officers actively and anxiously give out tickets to those who don’t. However, it is perfectly legal to ride in the back of an open-bed pick-up truck.” – Christine O., St Thomas USVI

“I get tons of messages from people who are looking for ‘real local food, off the beaten path’ so I recommend a few places, and like the old shampoo commercial goes, they tell 2 friends (TripAdvisor) who tell 2 friends, and so on and so on, and eventually they all complain that these locations are just ‘too touristy’.” – Laura W., Cozumel, Mexico

“Customers are the ones who must be the friendliest in order to obtain any service at all. Those working in the service industry are the ones who require the coddling.” – anonymous, somewhere in the Caribbean

“My husband volunteered to repair the police motorcycles at the new police station. One day, he was there working on a bike and asked for a Phillips head screwdriver. One of the inmates in one of the cells reached out and handed him one to use. They had LOCKED him up with his tool belt on.” – Deb C., Roatan Honduras

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“People tell me that I shouldn’t put my baby in her carseat because it will give her scoliosis, but they drive with their babies on motorcycles. Much safer.” Jen L., Dominican Republic

“Your ISP (Internet Service Provider) notifies you of an internet outage… via Facebook.” – Sophie, Tortola, BVI

“Sad but true – we are surrounded by water and a huge portion of the population does not know how to swim.” – Chrissann, Virgin Gorda, BVI

“High season for tourists is during our rainy season. They come to an island paradise in droves without realizing that we’re in the same hemisphere and therefore, it’s our winter too. I keep telling them to come back in the summer, but I guess they don’t appreciate the humidity-induced hairstyles as much as I do…” – Amanda W., Roatan, Honduras

“The internet is so slow, you can’t even open to check it.” – anonymous, somewhere in the Caribbean

“It is illegal to produce your own power (solar, wind, etc.), but the power company can’t provide uninterrupted power to a 13×3 mile island of ~23,000 people for more than 23 hours at a time. Not a day goes by that some part of the island isn’t without electricity!” – Danielle C., Tortola, BVI

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“Jimmy Buffett songs and the pictures they paint are often what inspires people to move to an island. Though once they’re actually living here, Jimmy Buffett songs quickly become the music they end up loathing the most.” – Chrissann, Virgin Gorda, BVI

“A cop told me I couldn’t have a beer bottle next to my volleyball court but there are drive-up bars. Apparently, drinking and driving is okay, but drinking and playing beach volleyball is way too dangerous.” – Jen L., Dominican Republic

“Everyone and everything moves on island time – until people get in their cars. Then, they race down the main roads (and not-so main roads), passing people on blind curves and missing oncoming trucks literally by the skin of their teeth, only to be foiled by someone who’s stopped ahead in the middle of the road to drop off or pick-up passengers. Not once in almost 9 months has someone passed us that we haven’t caught up with them less than a quarter mile later.” – Danielle C., Tortola, BVI

“Our cell phone carrier, LIME, has apparently partnered/sold ad time to the the DMV and sends out blanket text messages to all of their cell customers on the DMV’s behalf. One of the text messages we received? ‘Your whole life is in your hands. Look up! Don’t text and drive. A message from the DMV and LIME.’ Sent at 5:36pm while everyone is driving home from work.” – Chrissann, Virgin Gorda, BVI

lime text_WWLOR

“One morning, on the way to da boat, I passed a man on the street who mumbled something at me. I couldn’t make out what he said, so then he called me “focking rude” for not replying to his apparent “Good morning”. My bad, dude. Guess I’m the one who needs to work on my manners.” Stephanie T., St. John, USVI

“The bar is out of beer.” – Jen L., Dominican Republic

“You never wear make-up except for when you’re planning on re-entering the ‘real world’. You take the time to primp your hair and make-up for your big trip off the rock, enjoying the feeling of being a bit more put together than usual, only to make it to the boat and have a wave crash in your face, ruining your efforts in one fell swoop.” – anonymous, somewhere in the Caribbean

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Do you have some humorous examples of island irony on your rock? We’d love to hear them – add your input to the list in the comments below!

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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