A few months ago my wife and I paid $366 to sign our nine-month-old up for school in 2029. This is just to be put on a list, position unknown. A list that guarantees nothing but consideration to register at the school. The payment is non-refundable, and not put towards any future fees. There will naturally be an actual registration fee and deposit due if her position on the list entitles her to attend the school when we get closer to the time.

After procrastinating for months, including considering moving to multiple other countries instead of paying this ridiculous fee, my wife and I gave in and paid it. In return we got this:

Please find our payment receipt for your child’s 2029 registration fee attached to this email. As a gentle reminder this is not confirmation of placement but does secure her spot on the list.

Cheers!

Across these beloved Cayman Islands, mothers and fathers dig into their pockets and make this involuntary school donation because there is no other choice. School space is limited for our ever-growing population. You wouldn’t want your child left out.

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Caymanians who believe in the public education system can send their kids to government school for free. Technically everyone else can also send their kids to a government school but for a fee. $900-$15001 per annum plus external exam fees. That seems fair for the second most expensive place in the world2.

But due to very limited space, 46.7% of Primary School Children and 40.9% of high school children attend private schools.3 The high demand for education and low supply means the government must enforce a hierarchy of who gets placed first.

The admission hierarchy at government schools is: Caymanians and status holders first, then refugees and asylum seekers, then dependents of Caymanians, then dependents of government workers, then permanent residents, then everyone else if space allows.4 Space very rarely allows.

By not building enough public schools to meet the exploding population demand because, as then Finance Minister Rolston Anglin put it to a Finance Committee, the forecasting is “very unscientific,” the government has inadvertently created a market for eager capitalists to exploit. And exploit it they have.

Private schools currently charge anywhere from a whopping $18,000 to $36,0005 per annum with specialized support schools pushing that even higher. That’s a lot of money to give our little darlings an education, an education that they are only kind of, sort of entitled to.

The Cayman Islands Constitution doesn’t actually guarantee free education. Section 20 of the Bill of Rights says the government will “seek reasonably to achieve the progressive realisation, within available resources, of providing every child with primary and secondary education which shall [...] be free.”6 A sentence with so many hedges in it, it’s almost an apology in advance. We’ll try, if we can, maybe when there is money available, to move towards making school for all kids free.

In a country like Cayman, a wealthy developed tax haven, not a developing country, almost half the school-age population has no access to free education. Their parents, whose work permits and immigration fees fund a meaningful share of government revenue, do not even have the option of sending their children to public school.

I’m all for allowing the private sector to step in when the government can’t. Provide a premium service for those willing to pay for it. But with demand through the roof and supply short, basic economics means you’ll soon be selling your liver just so Johnny can learn to read.

There are of course consequences far beyond making expats pay through their noses to educate their offspring. The undersupply of government education, leading most expats to send their kids to private schools, could be inadvertently contributing to the us versus them dynamic that plagues us today.

People like to stick to what they know. I see it in Cayman all the time. People from the same country end up almost exclusively hanging out with other people from their country. It’s a disservice to yourself and the people of Cayman. But it’s human nature. Integration needs to be actively built into society or we will naturally stick to our tribes.

When kids share a classroom, their parents eventually end up spending a lot of time together. Time spent doing life with people is what leads you to discover that the person who looks different and comes from a different background is also exhausted, also proud of their kid, also trying to make the best life for their family, also winging it. You discover that we are more alike than different.

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I grew up in South Africa in a time when the country was actively trying to undo a system that had sorted people by race into separate classrooms, separate neighbourhoods, separate lives. Separating people sows distrust and animosity based on lies and hearsay instead of truth. It creates immeasurable damage. Damage that will take multiple generations to recover from.

By being in the classroom with kids who came from historically disadvantaged backgrounds, and then the lecture hall, and then the workplace, I learnt what the generations before me never could. These people that are different from me are just as smart if not smarter, they work just as hard if not harder and they have had to make incredible sacrifices to get themselves to the positions they are in today. They are just like me, maybe better.

Having a braai (BBQ) in each other’s homes, shouting for the same sports team, celebrating your commonalities and laughing at your differences. These are things that South Africa does well and has been the source of much of the healing that has taken place so far.

These are things that make a cohesive society. I want my daughter to have friends from every walk of life and every nationality on this island. To make real connections that will give her friends to visit in countries all over the world while also feeling comfortable to call this place home. Where the government has dropped the ball, parents will have to step up. We must actively reach across the divides to build the society we want our kids to inherit. All while coughing up $366 to get them on a list they just have to be on.

I walked out the office door and my wife didn’t waste a second breaking the news.

“The washing machine is broken.”
”What do you mean broken?”
”It doesn’t spin; it just starts counting down.”
”Ominous.”

An unfortunate but simply fixed adulting problem, right? But when you live in the second most expensive place in the world, which also happens to be an island, there’s no such thing as an inexpensive simple fix.

I set out to diagnose the problem. I’m a grown man. I have a degree. I can fix things. I was feeling empowered by recent successes with my trusty AI friend Claude, so I asked him for help. Claude walked me through which buttons to push to get a diagnostic error from the machine. The error apparently meant one of the circuit boards on the washing machine had given up under the weight of baby clothes and dirty gym towels. I quickly lost confidence in my abilities and decided to call in some ‘expert’ help to get the part replaced.

The ‘expert’ arrived on time, a shockingly positive silver lining in this saga, and after just ten minutes confirmed exactly the same thing Claude had already figure out. He then broke the bad news that Claude couldn’t. The part was not on island, it’s very expensive, and it would take weeks to get it here. Most of our neighbors with the same machine have already just replaced the entire thing. That’ll be $75. This guy should work for a consulting firm.

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My wife and I wasted a few hours in the island’s only giant hardware store considering our options while our daughter screamed to be let loose to crawl on the floor and whack the bathtubs indiscriminately. Do we bite the bullet and get something new? The dryer is on the brink of collapse too, with enough lint built up inside to label it a fire hazard. But none of the machines they have there can fit in our small apartment’s laundry closet. They didn’t have the part just as the ‘expert’ lamented. My wife and I go back and forth but given nothing is going to fit, and we want the fastest solution to a working washer we decide on ordering the part ourselves and flying it in. One week max.

I spend time online finding the right part and praying it’s the actual issue. Some kind friends allow us to wash our dirty underwear at their houses and we drag it home in bin bags to dry in our barely operational fire hazard. But when Monday rolls around I get an e-mail from the US parts supplier saying they have cancelled our order because they don’t ship to freight forwarders. We’re back to square one and the laundry is piling up.

During my Tuesday lunch break, we take a trip to the only other place on island that sells washing machines. We walk around the empty store as the salesman eyes us up without offering to help. We find a decent looking set of machines that will fit in our utility closet so we now need to engage with the salesman who has decided we’re not worth the trouble and has returned to his desk.

I don’t like talking to strangers so I urge my wife to ask him some questions. We walk up to his desk, preparing to spend way too much money on a washing machine and dryer. He doesn’t stand.

“Hi, what’s the difference between these two washer-dryer towers?”
“Not much.”
“O-K, so why is one more expensive?”
“It’s got some steam drying feature.”
“We probably don’t need that. Does it come with delivery? We live in town.”
“Delivery will be about $100…”
We literally live down the road.
“… and another $150 for installation. You’ll also need to buy some pipes for the washer and a plug for the dryer.”
“It doesn’t come with a plug?”
I finally join the conversation helpfully repeating my wife’s question, ”It doesn’t come with a plug!?”
“No.”
“And how much is that?”
“Probably another $60 for the plug and maybe $50 for the pipes.”

I’d had enough. I tell my wife we are just going to have to find another supplier for the part and for some reason we thank him before leaving. Now to be fair to the man we later found out it is normal for a dryer in North America to not come with a plug, but I can only tolerate so much madness before I refuse to spend money at a store ever again.

We went around the corner to their parts department where I had to look around and yell hello to find somebody to help us. The person quoted us almost three times the cost of the part we had already tried to order and told us it would take six weeks to get here.

When we got home we googled the price of the new machine we liked at Home Depot in the US. Less than half the price! Add in shipping from Miami to Cayman plus taxes, and we’d still be well below the sticker price at the local store. We gave in and I hit order.

No matter how long I live here I can’t get used to the terrible customer service stores in these beloved isles provide, making the sticker shock so much worse. Fancy hotels, who train their staff to smile through White-Lotus-level madness aside - residents frequently have to deal with surly, social media-scrolling staff. You’re made to feel as if you should apologize for trying to spend money in their store.

“I’m so sorry to interrupt your TikTok session Ma’am, but I really like the synopsis of this book. Would you be so kind as to let me pay you to leave the store with it?”
Grunt, teeth kiss.

I’ll be honest friends, these kinds of events have me feeling down about living in paradise. This saga started a month ago and our washing machine and dryer have only just cleared customs. We’re hoping it will be delivered tomorrow where I will now have to figure out how to install it because I refuse to pay $150-$300 for somebody to screw some things in for 30 mins. But God is good at reminding me when I’m starting to get ungrateful for my blessings.

Last week, my wife and I were enjoying an afternoon on Seven Mile beach. Recovering from our laundry woes and another round of washing at friend’s houses. Trying not to think about how much unexpected money we’d just blown. The weather was warm but not too hot, the water was beautiful, and our daughter was loving playing in the sand. Some tourists noticed my wife’s Canadian hat and struck up a friendly conversation. They were surprised to hear we lived in this beautiful place.

”Enjoy the rest of your vacation,” my wife said as they left.
”Enjoy your life,” they replied.

OK God, I hear you. Thanks for the perspective.

The lights are up on the roundabouts as the traffic grinds to a halt around them. The stores are playing the classics while the Christmas chocolates fly off the shelves. The hotel lobbies are filled with giant Christmas trees — one hotel even has a giant bow wrapped around the outside. The pastors are blowing the dust off their favorite Christmas sermons as they prepare for their highest church attendance of the year. The most wonderful time of the year is upon us in Grand Cayman.

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This year, to save us from tears, we decided to stay home for Christmas. Our little one — while up for an adventure — is still figuring out this sleeping thing which regresses tenfold when we travel. I’ve also got to work through the holidays. Study accounting they said… It’ll be rewarding they said…
Sadly that means we miss out on spending this happy time of the year with family. Playing board games with our nephews and opening presents together while snow falls softly outside is magical and will be sorely missed.

Before traveling to Canada for the first time, I’d never even seen real snow. The closest I’d gotten was some sleet in Dublin on a short visit. I’ve grown up with hot Christmas days, family braais*, eating cold meats and swimming in the pool at my grandparent’s place. Living in Cayman is more of the same. However, for my wife who grew up with snow and cosy fireplaces, a hot Christmas is still an odd experience.

*barbeques, South African style

To try and make the most of Christmas at home, and because it’s our little one’s first Christmas, we got a real tree and blanketed the floor beneath it with presents. The air-conditioner is on max, Christmas sweaters adorned, hot chocolates in hand, and a faux fireplace crackles through the TV. Turkey and all the spoils are ordered for Christmas Day. My wife has even been practicing my sister in law’s amazing stew so we can feel a little closer, even from across the world..

While many escape to Cayman to celebrate Christmas away from the cold, Cayman residents who don’t have large families on island will often head off-island to spend it at home. Those of us staying put celebrate together with our blended families. Families made up of friends, colleagues, and friends of friends.

It’s a special time of year to appreciate the blessings we have. May this Christmas be magical, no matter how or with whom you get to celebrate. For me, the beautiful traditions are a reminder of an incredibly gracious God, who provided the ultimate sacrifice for an undeserving world.

Merry Christmas

Over the last few weeks we’ve finalized our summer 2026 plans and started booking our flights. Summer in the Northern hemisphere is an expensive time to travel, so naturally my inner accountant was activated. A board meeting of budgeting neurons was called, the staff passionately stirred up to find creative ways to make this cheaper. Concluded with a bang of the calculator, the inspired neurons were sent off to fire away while I’m trying to sleep.

Airline miles, airline credits, bank points and deal-notifying Apps were rounded up and booking began. While we will normally jump at a good deal, we try to fly with one specific airline. They have some of the most convenient flights in and out of Cayman, and we have status so it saves us money with perks like free bags and seats.

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Unfortunately

this airline has a bizarre flaw in their booking system that does not allow you to book your flight with an infant in your lap. Instead you need to book a flight for two and then contact customer ‘service’ to add the child to your booking.

This ridiculous rigmarole which does not appear to be a thing on other airlines, means speaking to a poor sod who is following the most annoying script of long winded flattery. I prefer to use a text chat because I can’t stand holding a phone to my ear for long periods of time, listening to heavy headset breathing, or the worst royalty free music an intern could find.

Over the week I ended up chatting with multiple customer ‘service’ team members to add our daughter to multiple flights. I also had to use credits, another unnecessarily complicated task, likely in the hope you give up in frustration and never use them. I’m sure they have a high success rate.

After booking our last flight with points I began a chat one last time to have our daughter added to the flight.

The Last Conversation

starts with an over zealous greeting from Parikshit - not a made up name - filled with promise on how happy they will be to help. When they notice I am a status holder, thanks and appreciation are heaped upon me for my existence.

Being the efficient, non-chatty type, I try to get straight to it with what I need. Infant added to my flight that I should have been able to book myself, and all the information they need to make that happen. I jump in the shower while Parikshit gets to work.

When I get out of the shower, Parikshit has realized my flight was booked with points and asked if they can transfer me to the only person who can handle such a bespoke request. Instead of doing the transfer, Parikshit waits a few minutes for a response and decides to close the chat.

I start up the chat again, and just my luck get reconnected to Parikshit! I confirm that transferring me to somebody who can get my daughter added will indeed be helpful considering that’s the reason I’ve started this chat in the first place. They shower me with praise on my status and ensure me they are very happy to help before reviewing my previous messages and finally transferring me to Ravi.

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Ravi is also extremely excited to serve me, and is also very appreciative of my loyalty as a status holder.

They ask me to confirm the information I have provided only minutes ago to Parikshit, in messages they can apparently read. I repeat myself. He is thankful for the information.

As an aside I discovered over my many times going through this exercise with different team members that they can actually see what you’re typing in the chat BEFORE hitting send. How creepy is that!?

While Ravi gets to work on this complex task of getting my baby ticketed, he wants to know how my day is going so far. Considering I’ve spent three hours arguing about flight credits with previous customer ‘service’ team members I kindly refrain from answering that question.

Updates follow in five minute increments.

I’m assured that he is still working on it for me.
He’s contacting an ‘internal team’ — I thought he was the expert?!
I am thanked for my patience…
Again I am thanked for my patience… @#$%&!

Finally he confirms, “I have added the infant on your reservation, and you do not need to pay any fare for the infant.” Praise be!

“Your satisfaction means everything to us.” That seems highly unlikely Ravi but thanks for the heartfelt canned messages.

My P(doom)1 is probably on the high side—especially when I see companies replacing people with machines. But after experiences like this I say go ahead, let the robots have their turn. Lord save us all.

When eating in Cayman, similar to Manhattan, you’ll need to take a deep breath when the bill arrives. But as one might say when in the Caribbean, just keep yuh mind pon di real mission: enjoy yuhself an’ have a good time!

Here are my family’s favorites for a special treat:

Ms. Piper’s

Website; Cost $$; Family Friendly ★★★

Walk into a storybook tropical backyard. Hidden by palm trees and 7 Mile Beach hotels at the Hampton by Hilton, this beautiful garden restaurant mixes seventies vibes with an ever changing delicious menu. The tastiest, freshest salads you can find on island are, “inspired by seasonality,” allowing you to mix and match for a curated meal. Let the kids splash in the pool surrounded by pink umbrellas while enjoying their must-try lemonade or a beautiful cocktail.

Looking for more garden vibes? Every Bloomin’ Thing (EBT) Tea Room is Cayman’s take on a British garden center tea room. A great rainy day spot to try a selection of teas with your scone.

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Kaibo

Website; Cost $$; Family Friendly ★★★

Not everything is about the food, sometimes the location means so much more. Kaibo Beach, located in the district of North Side, was the landing site of Queen Elizabeth II’s historic visit to the Cayman Islands. “In her honor, a dock and beach hut were specially constructed.” The now evolved Kaibo beach has one of the nicest water side set ups on island. Sail up to the dock, grab an ice cold drink and wolf down a thin crust pizza with your toes in the sand. Service is hit-or-miss so go there with no rush and the food soon come. Something you can’t miss is their unmatched Tuesday night Barefoot Beach BBQ with fantastic live music. Catch the water taxi from Camana Bay and make it a night to remember.

VIVO

Website; Cost $; Family Friendly ★☆☆

Vegan, vegetarian, pescatarian, or just down for a delicious meal? Sneak below the right West Bay Dive Resort (Lighthouse Point) and you’ll find Vivo with nothing but iron shore between you and the ocean. We can be seen regularly driving by to pick up a Pad Thai (Asian rice noodles with vegetables, in sweet and sour peanut butter sauce) to go, but their Breakfast Burrito with a side of crispy seasoned potatoes will make you forget about meat entirely. The view and friendly owner led service makes up for the off the beaten path location.

If you’re looking for other healthy or vegan options, Island Naturals at the Grove has an extensive, mouth-watering menu. Our go to meals aren’t vegan but they are delicious. The Tuna Poke Nachos (Crispy Wonton, Avocado, Jalapeno, Radish, Wakame, Togarashi, Teriyaki & Sriracha Aioli) and Blackened Mahi Sandwich (Toasted Sourdough, Arugula, Smashed Avocado, Tomato, Pickle, Cilantro Lime Aioli).

Taikun

Website; Cost $$$; Family Friendly ★☆☆

World class Sushi in the middle of the Caribbean? Look no further than the Ritz Carlton’s Taikun. A beautiful setting for a date night - one of our favorites for special occasions. On top of the most delicious Sushi you can get on island, the Ritz is one of the few places on island with consistently amazing service. The Yellowtail Jalapeño is a personal favorite (Hamachi, Lemongrass Ponzu, Valencia Orange, Jalapeño) and you have to try the Bonsai Tree if you have space for dessert (75% Madagascar Mousse with Salted Caramel Crèmeux and Matcha Green Tea Sponge). For the meat lover, their signature Wagyu Beef Nigiri (4 pieces - Wagyu Beef Nigiri, Garlic Chip, Scallion, Japanese BBQ Sauce, Wasabi Mayonnaise) is incredible.

Grand Old House

Website; Cost $$$; Family Friendly ★☆☆

Historic colonial charm on the water. Perfect for an anniversary or impressive date night, this restaurant has special meaning to my wife and I. Watch the sunset over the South Sound water while eating an incredible meal paired with wine from their extensive wine collection. Start with the Local Fish Ceviche (citrus juices, yuzu, peppers, tomato, onion, cilantro, jalapeño, avocado, corn chips), share the Chateaubriand (center cut of beef tenderloin, flambéed and served table side potato gratin, green asparagus, roast vegetables, red wine jus, sauce bearnaise), you’ll have no regrets.

Coccoloba Bar

Website; Cost: $$; Family Friendly ★★★

One of the most stunning locations to catch a Grand Cayman sunset. Let the kids play in the calm seven mile water, while you sip on the island’s best Pina Colada and munch on some fresh ceviche from the Mexican Street food bar. Our favorites include the Elote Appetizer (grilled corn, tortilla crisps, cotija cheese, lime, chipotle aioli) and Red Chili Pork Tacos (kimchi pork belly, spicy mayo, pickled red cabbage). It’s not only great for the humans, dogs are welcome too with their very own menu. This is our pup Charlie’s go to place for his birthday, adoption day and any other excuse we can come up with for a puppy inspired celebration. Pop in on Mariachi night for a good time, just make sure your dog isn’t scared of sombreros.

Seven Mile Beach Special Mentions. If you’re looking for some more Instagram worthy locations on Seven Mile Beach - Bonny Moon, just a few steps down the beach, leans into the upscale drinks and party vibes when the lights get low. They also have great tables on the beach when beach erosion hasn’t washed it away. Or if you’d like to bump elbows with celebrities and eat fantastic steak with your toes in the sand, Tillies has less ocean view seating but incredible food.

Carnivore

Website; Cost $; Family Friendly ★☆☆

Sadly, my favorite burger spot on island closed this week. It’s what inspired me to write about my favorite food spots on island. Carnivore was a premium butcher in Camana Bay that would cook any meat from the Butcher’s case and serve it to you right there. For those of us lacking any kitchen skills this was one of the best deals you could be offered. I’m going to miss this spot so much, especially grabbing a steak sandwich to share on the run on busy nights.

While Carnivore may be gone, the Carnivore Smash food truck lives on. You’ll find me there wolfing down a Tropical Heat Smash Burger (seasoned smash patty, melty American cheese, shaved onion, grilled pineapple, creamy coleslaw, jerk BBQ sauce and a kick of scotch bonnet aioli).

All of these places not only have great food, locations or both; they have many special memories with friends and family. For all of human history, eating together has been at the heart of our social fabric. Restaurants that attract us with amazing food are really just a great excuse to make memories with people we love.

Cost Meter

• $ - Standard Cayman Eating Out Prices

• $$ - Above average Cost

• $$$ - Expensive, even for Cayman

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