The Pros & Cons of Expat Island Life

The Pros & Cons of Expat Island Life

If you had told me a couple years ago I would be writing a blog post about expat island life, I’d think you were crazy. That maybe you’d been hit on the head with a coconut. “Me? Living in the Caribbean? Get out of here!”

But then again…I do love the beach…. And year-round summer does sound pretty nice…

Cut to the chase, here I am living my best life on a rock in the middle of the ocean. Although, it’s not all rum punches and rainbows. After a year of uninterrupted island life, I’m here to share with you the ups and downs one can expect to encounter when uprooting their life to the Caribbean. 

The pros and cons I have generated for this blog post are honest and come from my completely unique perspective. Of course there will always be people who live a distinct experience from my own. My aim in writing this is to share a bit about my island lifestyle, showing two sides of the same coin in a light-hearted way. I hope it makes you smile and remember to love where you live, whatever “home” currently looks like for you! Without further ado, here are The Pros and Cons of Expat Island Life according to Island Diaries by Kate!

Pro: Rock a tropical wardrobe 24/7

Where I’m from we keep totes of winter, spring, summer, and fall clothes stored away under the stairs in the basement. Every year the short-shorts and tank tops anxiously await their return to the limelight for the fleeting months of summer. Just imagine the weight that would be lifted off your shoulders if you only had to plan for one season…summer! This is exactly what it’s like to live in the Caribbean, where the forecast is always sunny and 86 and flip-flops are widely accepted. I like to refer to this wardrobe as “tropical minimalism.”

expat island life

RECOMMENDED READ: What to Wear in the Cayman Islands

Con: The “Groundhog’s Day” effect

Sure, sunny and 86 sounds dreamy but when this is the weather EVERY day, it starts to get old. It’s kind of like “Wow, gorgeous again? How original!” I often find myself fantasizing about brisk fall mornings that call for a sweatshirt and a warm cup of coffee. Cayman does have a rainy season which makes the weather slightly more interesting and unpredictable, but it doesn’t quite compare to experiencing all four seasons and the activities that come along with them. 

Pro: Amazing friends from all over the world

This tax haven, with its white sand beaches and turquoise waters, attracts young professionals from all around the globe. My first few months in Cayman felt like studying abroad all over again. Within a matter of weeks I had friends from England, South Africa, Colombia, Ireland, France, and the list goes on and on! The diverse social dynamic lends itself to an instant-friend phenomenon. One minute you’re chatting it up with a stranger at Starbucks and the next you’re invited to their boat party. The expat social networks in Cayman are very much intertwined meaning you undeniably have a mutual friend with every single person you meet. 

expats cayman islands

Con: Expat “bubbles”

There are so many opportunities to make friends with other expats but not nearly as many to make friends with locals. Undoubtedly this is because my apartment and almost all my favorite activities are in the Seven Mile Beach area which is heavily populated by expats. These enclaves contribute to a feeling of separateness from the local community. While it’s okay to be separate in some ways, I do feel I am missing out on many important cultural aspects by keeping within my “bubble.” 

Pro: No taxes

Self-explanatory. There is no question that this is a MAJOR pro of living in the Cayman Islands!!! (Thanks John Grisham for the inspo).

RECOMMENDED READ: 25 Weird Things That Only Happen in Cayman

Con: $10 peppers (the price of paradise)

We may live tax free but that does not save us from extortionate supermarket prices. There are many fruits and vegetables I’ve had to give up altogether while living in Cayman. For example, peppers. A single yellow or red pepper could cost you up to CI $8 which would be close to USD $10. Same with Romaine lettuce and almost any kind of berry. I’ve resorted to buying most of my fruits and vegetables frozen or in a can. Of course, we try to buy local produce when possible at the farmers market or at roadside stands, but sometimes you just want to indulge in a raspberry without breaking the bank! Is that too much to ask??

Pro: Short commutes

Of course, this depends where you live on the island. But, since I live in the Seven Mile Beach area, many of the restaurants, beaches, and supermarkets are either in walking distance or a few minutes drive away. Yet somehow, even with these short distances, I still seem to arrive everywhere late. I guess “island time” can affect even the most punctual of midwesterners. 

The furthest I have to drive is 15-20 minutes to get to the school where I work. When I tell Cayman residents this, they are taken aback by the “lengthy” commute. They clearly have never experienced 40 minutes of interstate blizzard conditions in the dead of a Minnesota winter…

expat island life

Con: No such thing as a “road trip”

Yes, I love being close to everything. It makes it super easy to organize plans on the fly. One thing I really miss though, is being able to take a road trip. I miss downloading podcasts and playlists and just hitting the open road. Even if the final destination was just to my hometown, it was the feeling of freedom that came with knowing a full tank of gas could take you anywhere. Here a full tank of gas gets you 45 minutes down the road to Rum Point where you can see… yup you guessed it, the ocean!


Pro: Endless island activities

And I do mean endless. Diving, snorkeling, boating, beaching, brunching, ahem–drinking, you name it! Cayman’s social networks are well-connected and VERY active. Because most expats do not have family here, our social calendar is typically wide open. (Minus the auditors who get let out of the office only for their required 4 hours of sleep) This leads to busy weeks and jam-packed weekends. Of course I enjoy the occasional chill weekend, but for the most part, I love having all of these social options. It helps to create a sense of community while we are all so far away from our families. 

scuba diving grand cayman

Con: Missing out back home

The Instagram stories tell one story, but of course, we all made sacrifices to live the picturesque island life. I think all island expats experience homesickness to varying extents, especially this past year as very few of us were able to leave the island. I went through a period where seeing planes take off from the airport made me want to cry. (Very dramatic, I know). It’s hard to miss out on celebrations and holidays and watch your baby nephew grow up through technology. (But thank god for technology). For sure this is one of the biggest cons to living abroad, further amplified by COVID restrictions this year. 

Pro:  Finally becoming a “regular

As silly as it sounds, I have always dreamed of becoming a regular at a café or restaurant. Of course you can become a regular no matter where you live, but the island’s small size and interconnectedness encourages the formation of rituals and routines. After living for a year on the same tiny island, Bryan and I can proudly say we are regulars at Palm Heights where we spend a good chunk of our paychecks on Paradise Pizzas and cocktails from Tillie’s. (Worth every penny!)

tillies, grand cayman

Con: Everyone knows everyone

The small town effect is inescapable. As mentioned above, this can be a good thing…but it can also be an annoying thing. Trips to the grocery store may take double the time because you could run into 10 people you know. One time I actually wore a baseball cap (very low over my eyes) and headphones so that I wouldn’t have to talk to anyone. It’s wonderful to feel connected but sometimes you just want anonymity when you’re contemplating your apple options. 

Pro: Palm trees and white sand beaches…

Sorry for stating the obvious, but this is a pro that cannot be ignored. Some days I wake up and think, damn, I live in the Caribbean. I feel extremely spoiled to be able to go on beach walks and sea swims whenever my heart desires. I will never get tired of watching the sunset from Seven Mile Beach. And even after a year of island life, the palm trees have yet to lose their magic for me!

cayman islands

Con: We’re literally in the middle of the ocean

When you move to a tropical island, you must learn to roll with a certain level of inconvenience. While Grand Cayman is blessed with numerous resources, it is certainly not overflowing with choice. The only “clothing” store I feel comfortable spending money at is the Humane Society Thrift Shop, everything else I’ve found is overpriced and/or not my taste. You may think, but Kate, why don’t you just ship things to the island? Well, many people do. But weeks of waiting and extra customs fees are just not worth it to me. Bryan was without a car for almost 2 months as he awaited parts from overseas. I dream of the day I can walk into a Target again or make a next-day Amazon order! Long story short, if you are someone who prioritizes convenience, don’t move to a Caribbean island. 

cayman islands, expat life

Pro: Personal growth and expansion

Moving abroad is an experience which will shift your mindset and pull you out of your comfort zone. Cayman, with its diverse population and unique geographical location, provides an especially expansive environment for personal development. Living the expat island life has taught me to value many different perspectives from locals and expats alike. Also, being immersed within inspiring tropical nature and a slower-pace of living has given me so much peace of mind and space for creativity. This year has inspired me to pursue my passion for writing in the form of this blog and has allowed me to connect with many ambitious and open-minded individuals. I am so grateful to the friends I’ve made this year as they have shown me many different possibilities for my own career and lifestyle. 


 So while living the expat island life is beautiful in many ways, it does not come without its share of challenges and inconveniences. Just remember that someone’s Instagram feed is a highlight reel, never the full story. No matter where you live in the world, you will find things you love and things you may like to trade. The key is to focus more on what lights you up rather than complaining about things that are out of your control. I hope you enjoyed this read and that is broadened your perspective on island expat life! 


 Hi, I’m Kate! I’m a Wisconsin native who traded her snow boots for flip-flops in May of 2020 when I packed my whole life into two suitcases and moved to the Cayman Islands with my partner, Bryan.  I created Island Diaries as a way to document my island adventures and share about the Cayman lifestyle. A Midwest girl at heart, I bring a fresh perspective to Caribbean life, serving as a guide for locals and tourists alike on all things Cayman Islands. Whether you are local to Cayman, planning to visit, or just curious about island life, I invite you to explore Island Diaries and let this site guide you on your next island adventure!

Latest from the Blog

10 Words You Should Know If You Live in Cayman

In my first year of writing this blog, I wrote an article about all the UK words and phrases I had learned in Cayman. Some people loved it, some people were annoyed by it. Caymanians…

2 Days in Viñales: Stories from the Cuban Countryside

Cuba is the largest island in the Caribbean, stunningly diverse in both its geography and lifestyles. To have a more complete picture of the country, you have to travel outside of Havana. One of the…

The Traveler’s Guidebook to Havana, Cuba (2023)

My first trip to Havana was a long time in the making. I have wanted to visit ever since meeting my husband, Bryan in 2015; it’s where he was born and spent the better part…

Get new content delivered to your inbox!

25 Weird Things That Only Happen In Cayman

25 Weird Things That Only Happen In Cayman

State the obvious, Grand Cayman is a Caribbean paradise and a wonderful place to both live and vacation. However, its beauty and prestige do not make it immune to some unavoidable quirks and peculiarities. I feel the longer one lives in Cayman, the less noticeable these oddities become. However, as a Midwest girl laying fresh eyes on this undeniably unique island, I have observed some truly one-of-a-kind occurrences that are too good not to share! The 25 items below are things that have surprised me, amused me, or just plain stopped me in my tracks since I have moved to Cayman.

1. Island residents pay hundreds (probably thousands) of dollars to stay at hotels that are 10 minutes from their own home. AKA Staycationing, somewhat of a COVID-inspired phenomenon. 

2. Ordering anything from overseas pretty much guarantees several weeks or months of waiting. That is, if it even arrives.

3. ALL supermarkets (and many stores) are closed on Sundays meaning weekly errands have to be completed on Saturday. Oh, the horror.

4. The island’s dump (Mount Trashmore) is located in plain sight and is literally the highest point on the island. Once a year it starts on fire and CIS has to cancel school because of the fumes.

5. People feed and pet wild stingrays like they are puppies. It is even considered good luck to kiss them.

6. There is such an overpopulation of green iguanas that people actually go “iguana hunting” for a cash reward. Before you get too excited, I think the reward is only $5 per iguana.

When in Rome?

7. There seems to be no system for returning shopping carts at the grocery stores. If there is one, no one is following it. As a result all the carts end up strewn throughout the parking lots, at bus stops, and on the side of the road. Yes, I am upset about it.

8. Driving 45 minutes to the other side of the island is considered a “get-away.”

9. In the 2+ years I’ve lived here, I’ve never had a personal mailbox. No junk mail. No bills. Everything is either dealt with electronically or mailed to my employer.

10. There is no televised new station in Cayman, but rest assured, there are still a wide variety of news outlets. The most popular, in order from most reliable to pure gossip are as follows: Cayman Compass, Women of Cayman Facebook Group, and Cayman Marl Road. You should follow all three for a well-rounded perspective 😉

11. On any given moment it could be torrentially raining in one area and blue skies one minute down the road.

12. Nowhere else in this world is there a Tony the Mango Man. And nowhere else on Earth do the mangos taste quite as good!

13. At first I thought it was a tall tale but apparently people actually cook turtle meat and put it in a soup called Turtle Stew. 

14. Gaelic football, despite its inane rules, is the most popular sport for expats on Island.

15. The famous, award-winning 7-Mile Beach is not actually 7 miles at all, it is about 5 and a half. But you can walk the entire length of it which is pretty awesome.

16. The right of passage for new island arrivals is to attend either a boat party or a brunch (probably both, many times over). Oh, and be recruited to play Gaelic football.

17. Chickens. Chickens everywhere. On the golf course, in the streets, at outdoor restaurants, at the beach, and anywhere else you can think of. They will be there…asserting their dominance.

18. People are very quick to tell you exactly where they live. The island is so small, it’s nearly unavoidable.

19. Paying $2,000 per month for rent is considered a “good deal.”

20. It’s been over two years and I’m still not sure where to buy underwear on this island.

21. A bag of romaine lettuce costs $9. *GASP!!*

(7.69 CI = $9 US)

22. The “Christmas Breeze”: Around December and January, the temperatures in Cayman drop ever so slightly and everyone rejoices!

23. There are over 40 dive operations and 365 dive sites. There is literally a dive site for every day of the year

24. NO TAXES 😉 (but the money you save in not paying taxes goes straight to your romaine lettuce budget)

25. There are as many Hondas as there are people. That’s an exaggeration, but sometimes it feels that way.

As you can see, Cayman is quite a unique little island! It goes to show even tropical paradises are susceptible to certain eccentricities. But just like anywhere else in the world, the longer you live somewhere, the more these things become ingrained in your worldview. Cayman is an island that inconveniences its residents in some ways but spoils us in so many others! If you can get past the chickens and the $9 romaine, I think you’ll find it’s a pretty fabulous place to live.

Where to Shop in Cayman: Spacie Store | Trendiest Island Looks

So you have an upcoming event…maybe it’s a brunch, a boat party, or even a long weekend getaway. You’re so excited until you remember…you have nothing to wear! We’ve all been there. In Cayman, this wardrobe crisis is multiplied by ten, given the shortage of cool and affordable clothing stores. We’re living in the land…

Discover Cayman Brac: Where to Stay & What to See

There is nowhere quite like Cayman Brac. It has a beautiful kind of quirkiness that manifests itself in the radical kindness of the locals and the peculiarity of the island’s “attractions.” These traits are juxtaposed against a gorgeous Caribbean backdrop, leaving you wondering if Brac is even a real place. Maybe I dreamt it all?…

5 Amazing Spots to Grab a Drink in Madrid

Visitors of Madrid are like kids in candy stores. The city is teeming with terraces and tapas bar, each one offering a unique kind of allure that only the madrileños can pull off. With so many options, it can be hard to know where to start. Read on and narrow your search, discovering 5 amazing…

Boggy Sands Road

Cayman Lifestyle Guide

Things to Do in Cayman

grand cayman stingray city

My Story: Moving to Cayman

Brooklyn Bridge

Off-Island Adventures

Get new content delivered to your inbox!

Running The Cayman Islands Marathon

Running The Cayman Islands Marathon

What kind of crazy person gets up at 2:30 am to run a marathon on a Sunday? The answer, of course, is ME! Well, me and a thousand other Cayman residents. And although I believe the use of ‘crazy’ here is somewhat justifiable, I have to say to you, don’t knock till you try it…there may just be a method to this madness!


My Sunday did in fact start at 2:30 am. That is what time I rolled out of bed and began my race day preparations. I would be running the Intertrust Cayman Islands Half Marathon, an event I had trained for throughout all of November. I was ready — nothing could stop me! Not even the ungodly start time. 

The day before the race I stocked up with all my supplies — organic running gels and electrolyte drink mixes from Be Well Pharmacy and most importantly, coconut water (from the not-so-fancy gas station). My breakfast consisted of Ezekiel sprouted flax bread (AKA magic bread) and a fried egg. While this was being prepared I started in on my liquids — black coffee and a lemonade electrolyte drink. I know what you’re thinking…that combination would probably land you straight in the porta-potty. I know what works for me but that does not mean it will work for everyone! We must tread very lightly with our pre-race meals…

Tip: The morning before a race you want to stick to foods you KNOW you digest well…likely a familiar food in your diet. If you’re going to consume as much as I did, you need to get up early enough for your body to digest it! (2-3 hours prior to the race)

By 3:30 am I was loading up my scooter getting ready to hit the road. Under the seat I stored by race day bib along with my running belt and bag. I laced up my Asics, fastened my helmet, and eased my scooter onto the empty highway. I felt like Will Smith in I Am Legend as I cruised down a eerily silent West Bay Road en route to Georgetown waterfront…not a vehicle or pedestrian in sight.

Upon arrival at the waterfront, I was still getting ghost town vibes, but as I turned the corner toward the start line I began to hear and feel the unmistakable race day buzz as fellow runners and volunteers milled about to DJ beats. The clock counted down to 4:30 am, the official start time for all marathoners and some halfers. Despite the absence of spectators (due to COVID restrictions), everyone was in very high spirits, ready to race against the sunrise along the Ironshore. I checked the zipper of my running belt, adjusted my Bluetooth headphones, and queued up my unbeatable motivational Spotify playlist. Time to do the damn thing!

Tip: If music motivates you while running, make a playlist that lasts as long as the run itself. Give yourself a little leeway, but not much. I made mine exactly 2 hours in length. I told myself I HAD to finish in under 2 because god forbid I run without music. Song choice is everything! I choose only music that has meaning or pumps me up (ideally both).


At exactly 4:30 am our large running pack pulled away from the waterfront and started down South Church street with direction to Sound Sound. Lighting was sporadic, leaving stretches of darkness illuminated only by the starry sky. Luckily, the weather was perfect and we enjoyed the slightly cool morning air…(I’m still a Midwesterner, so cool to me means 40 degrees).

While there were no spectators allowed at the start and finish, the volunteers at the refreshment stations and the die-hards standing on the side of the road at the crack of dawn really made up for it. After a few miles of people yelling “Go Kate!” I realized that I was not as popular as I thought and that my name was printed large and bold on my race bib.

We ran all the way through South Sound, past Hurley’s, and finished the loop at the end of Old Prospect Road, actually running right past my school before hitting the halfway point. I did not think I would be a fan of back-tracking the whole course, but actually it was fun to be able to see who was leading the pack and who was following closely behind. 

If you have never taken part in an organized running event, it is something you absolutely have to attend. Either as a runner or a supporter. There is something so completely unifying about the experience. Endurance running is an activity that we have been taught to dread but  it is actually one of the most natural instincts we have as humans. It brings us back to our hunter-gatherer days when we had to chase prey over long distances without a break. While a marathon is not nearly as purposeful as what our ancestors had to do, I believe it still brings us closer to our roots and helps to eliminate social divide. As corny as it sounds, it feels so good when a random stranger cheers you on and says YOU CAN DO IT! No joke, I got goosebumps probably ten times throughout the race…the runners high is a real thing.  If you don’t believe me, go experience it for yourself! At the very least, you will get some free food and beer at the end. 


With amazing supporters, a straight fire playlist, and quite favorable running conditions, I was able to maintain my goal pace of 8:30 miles throughout the whole race, putting me in a position to break my personal best! Winding through the streets of Georgetown, under a cotton candy sunrise, I neared the finish feeling exhausted but elated. I crossed the finish and was immediately adorned with a finisher medal. Just like that, it was over!

I made a beeline for the free food, selecting without any hesitation a bag of Famous Amos cookies. Nothing ever looked as heavenly. I ate my cookies with the satisfaction that I had definitely earned them. I mingled about with some other runners and tried not to fall over. Because of COVID restrictions, we couldn’t stay at the finish for long. After snapping some pictures and finishing my snacks, I made my way back to my scooter and cruised away toward Seven Mile. I looked at my watch…it was only 7 am. 

In true Cayman fashion I went straight to the ocean after my run. The water is actually “chilly” at the moment as temperatures have dropped a bit and we are experiencing what the locals call a “Christmas Breeze.” I’ll take what I can get. Anyway, this cool water felt pretty much amazing on my muscles and joints. 

After a morning of running and swimming, I basically felt like Iron Woman. This feeling didn’t last for long as I collapsed into bed and slept for 2 hours…getting up only because we had brunch reservations at the Kimpton. 

If ever there is a day you are entitled to an overabundance of fancy food, it is following a full or half marathon. It is essentially the 21st century equivalent of catching and eating your prey after a 13 mile chase. (I am only kidding, of course.) The other girls at brunch had also run the half marathon and we took our brunching very seriously that afternoon. 

All in all, it was one of the best days I have spent here in Grand Cayman. If I haven’t convinced you to run in the next Cayman marathon…or any marathon at all…hopefully I have at least convinced you to come cheer on the runners! Or at the VERY least not call us crazy 🙂

Thanks for reading! If you have any questions about running in Cayman or running in general I would be so happy to answer!