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!

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