The Cayman Islands are a cluster of 3 islands with 3 different personalities; Little Cayman for those who want to unplug, Cayman Brac for those who want to visit the Bluff, and Grand Cayman for accountants, partiers, cruise ships, beaches and everything in between.  We may get a bad rep of being evil money launderers thanks to The Firm and any other TV show about white collar criminals, but we are so much more than that false representation.  What makes Cayman such a unique place is that our lifestyles are formed by both locals and expatriates with the ratio being 50:50 at this point. Once you join our small community for long enough you’re bound to experience these quirks of living in the Cayman Islands.

1) Dating

Over the years, I have watched many expats move to the island in relationships, and then also watched a lot of them fall apart.  It seems that many don’t expect to be tempted here, but the mixture of locals and foreigners (some being from their own homeland) makes things tricky. It’s basically an episode of Temptation Island where you start off together and after a few weeks you’re hooking up with the guy or girl in your newly formed friend group.  As a local, I can’t complain because having more choice is vital to ensure that you minimise the chance of dating your cousin.

2) The seriousness of conch & lobster season

One of the perks of living in the Caribbean means that you get your fill of fresh seafood, right? Not in the case for conch and lobster. Both have their own season to prevent overfishing and ensure that these creatures can grow large enough for us to really enjoy.  Conch and lobster lovers get a bit too excited when the seasons kicks off, so it’s no surprise that a few colleagues are ‘out of office’ day one because they are busy hunting for their dinner.

3)  A 15 minute drive is “too far”

It’s always been an issue to see friends if they’re more than 15 minutes away from you.  As a local, I’m obligated to take the long drives because my mom lives 30 minutes away, but even those trips are few and far between.  With friends it is definitely not happening for them to come by and visit your home if you are more than 15 minutes away.  To get around this debacle a local bar or café is chosen that’s equidistant for everyone involved.  Expats who move to the island from big cities with hour long commutes think it’s a ridiculous notion initially, but it only takes a couple months for them to conform and leave the city mentality behind.

4) Making the most of our Weekends

Knowing how to navigate the weekend in Cayman is one of the hardest things to understand when you first move to the island.  It looks a little something like this:

•Friday: work is done and it’s the only night you can let loose til 3am.
•Saturday: this is the only day to do errands because after today the banks, supermarkets, retail shops and liquor stores don’t open again until Monday. You may be questioning why you went so hard on Friday when you had a list of tasks as long as your arm to complete.  The evening doesn’t get much better for night owls because bars and clubs must be emptied out by midnight because 12:01am is God’s day.
•Sunday: the integration of church and state is a key component in understanding Cayman. So you may head to church, but afterwards it’s time to make the most out of your Sunday Funday before the work week starts again.  With everything shut down besides bars, restaurants and gas stations your options are limited to boozy activities, staying at home to do housework or heading to the beach.  Believe it or not, we seem to be stuck in the time of Footloose because no “live music” is allowed and you can’t show rated R films at the cinema.

5) Less than a dozen stoplights, but tons of roundabouts

Cayman was a built on a basic road system where originally one road followed the coastline from one side to the other.  As we’ve become more developed and bypasses (highways) were introduced, the government decided that stoplights or 4 way stops were not going to be effective, so they jumped onto using roundabouts.  The problem with roundabouts is that everyone has their own idea of how they work and adding tourist drivers into the mix doesn’t help the situation.  Now we have introduced 3-lane roundabouts and knowing how poor the driving was before, they’ve painted arrows on the road to make it easier to understand. Surprisingly everyone still gets it wrong and my only advice is to stagger, just in case the idiot next to you decides he feels like going all the way around using the outer lane.

So there you have it.  The Cayman Islands, a place of beautiful beaches and stingrays, but also one of drama, short drives and no live music on the Lord’s Day. If you’ve been before have you noticed these island quirks?


Written By:

Current Rock of Residence:

Cayman Islands

Island Girl Since:


Originally Hails From:

Cayman Islands

Chelsea comes from the island of friendly stingrays, powdery beaches, top notch cuisine, epic scuba diving, and all-you-can-drink brunches. Growing up in the Cayman Islands sounds like a dream, but she always wanted to see what city life was all about. She got her wish for a total of 8 years when she pursued her Kinesiology and Physiotherapy degrees in Canada and Scotland, respectively. She never stayed away from Grand Cayman for long as her regular school breaks allowed her to come home for every roasting summer and breezy winter.

When she finally left Glasgow in 2013, she dove headfirst into the work hard, play hard mentality of island life and has never looked back. She’s a full-time physiotherapist, but is also passionate about promoting Cayman’s culinary scene through her food & travel blog, Island Epicurean. Chelsea uses her Caribbean and worldly upbringing to share stories about the quirks, drama, and hilarity of life in the Cayman Islands. You can also find her on Instagram.

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