Whether you’ve already made the big decision or are still letting the idea of a more permanent island escape tantalize your imagination, there are some looming questions you surely have.

One biggie for me when I decided to jettison my old life for the land of umbrella drinks and cabaña boys was…”What should I pack?”

As this was going to be more than my usual vacation in paradise, my mantra of bikinis, cute cover-ups and high-heeled sandals (just in case) wasn’t quite going to do it. Standing in my former home in the PNW, gazing around in the weeks before departure, I was staring down three decades of accumulated possessions.

Clearly, everything could not make the cut – nor should it. After all, there is little need for a single Northface fleece pullover (let alone four) in the land of perpetual heat and humidity. Same with my backcountry skis. Or my collection of fashion boots and designer handbags (yes, I did bring a few favorites, but eventually they succumbed to this inexplicable closet conundrum).

In hindsight, of course, some of the things that did make the cut are a bit questionable. Christian Dior stilettos? Two pairs of ski goggles? A black feather boa and pair of large black angel wings? I’m sure these seemed like “must-have” items on the cold, dreary Seattle afternoon when I crammed five shipping boxes full of my “essentials.” But once installed on my rock? I am still shaking my head on those items.

The struggle is real.

Except, to be fair…the boa and wings came in handy at the first Halloween party I attended. Costume tip: A naughty angel, especially one the island’s male population has not yet met, is always a fan favorite.

Of course, with the benefit of seven years of island life under my belt, I’m confident that my packing list would look a little different – and a lot lighter – if I were doing this again. After all, experience is the best teacher. And I’m a quick learner.

So benefit from my hard-learned lessons, people. These are the three essential items you must pack when you move to the islands.

An Open Mind

Guess what? As shocking as it may be (although it really shouldn’t be), island life is not going to be the same as life as you knew it in the “real world.”

But wait…before we go any further…let’s dispense with that “real world” vs. “island world” categorization, shall we? The minute you voluntarily choose to live on a tropical island, the island becomes your real world. Continuing to proclaim things like “back in the real world” is no longer accurate. Or cool. Funny sometimes, yes, I mean…see this blog. But saying it as a means to convey the humor of the situation and seriously believing it are two different things. Unfortunately, the latter occurs. More than you can imagine.

Also, you won’t make many friends (either locals or the long-term expats) if you say stuff like that out loud.

You see, long before you arrived, all those island folks were living in the real world. It just happens to look different than yours (and have a nicer climate). These folks managed just fine to exist without your presence, advice, opinions or unintended insults. They had the island versions of grocery stores, banks and shopping options, and managed to make do with them all. Imagine that. So insinuating that their valid existence is, somehow, not “real” might be perceived as slightly insulting.

At the end of the day, we are all just interlopers into these amazing spaces. Even those who have clocked decades on a rock. It is a privilege, really, to live here at all (especially in immigration’s eyes). So act like it. Be a transplant people actually want on the island.

This means, painful as it may be, you have to bite your tongue and accept that things happen in ways you will never understand. It also means, under no circumstances should you raise your voice, stomp your feet or argue with anybody in charge. Ever. Likewise, no matter how ridiculous you find things (and you will…I still do on the daily), the only legit thing to do is smile and let it pass. At the post office. At the grocery store. Anywhere in public, basically.


Of course, this doesn’t preclude you from going home, mixing a strong cocktail and commiserating with other island girls and boys about your frustrations privately. After all, isn’t that what WhatsApp is for? Just never do your venting in public. You can also read this blog (the contents of which are always offered in a tongue-in-cheek manner, by the way…lest there be any confusion).

Long story short…it seriously pays to approach every new situation as a chance to broaden your horizons and discover alternate ways of doing things. After all, you are not moving here to re-create your life back home, are you? Embrace the differences. Invite them into your head and heart. Having an open mind is the first step towards successfully integrating into island life and making friends.


Ok, I don’t want to burst anyone’s bubble, but…your arrival on the island is not the saving grace we’ve all been waiting for. Fresh produce? Yes. You? Not really. Believe it or not, others came before you who (a) achieved similar levels of education, (b) had really important jobs back home, (c) maintain similar amounts in our bank accounts or – gasp!! – (d) all of the above.

This seems like a no-brainer, right? I mean…just think about how many former doctors and lawyers are now bartenders, dive instructors, boat captains and musicians on rocks around the world. A lot. Alas…day in and day out I see new arrivals acting as though they are the first to arrive with any intelligence, common sense or wherewithal to get shit done here.


The first thing to do after unpacking is NOT to introduce yourself to the local population by boldly proclaiming that you’re going to single-handedly change everything that is wrong (in your view) on the island. Even worse if such proclamations are accompanied by a smirk as you gaze at seasoned transplants (like myself), clearly wondering why the likes of us haven’t already solved all these problems. Obviously, we’re all stupid. Or lazy. Or drunk. Or all of the above.


Your island integration will be much smoother if you just take a deep breath and get to understand the lay of the land before you start shooting off your mouth. Stop, look and listen and many secrets will be revealed – about who is who on your rock, why certain things work the way they do and what is likely changeable (and not).

Give yourself a few months to experience the reality of day-to-day life here, and you might even understand that we are all not just booze-addled miscreants hiding out in the tropics (regardless of what our appearance might suggest). Some of us are, of course, but the majority are not. Rather, we understand that the fastest way to accomplish something here is slow and steady rather than guns blazing. Plus, frankly, it is too damn hot to move fast anyway.

When you are tempted to believe you know it better than those who’ve been around much longer than you, I strongly encourage you to check your ego before you utter a word. Nobody likes a know-it-all, and that is especially true on a rock.

Who knows? You might have a kick-ass idea and it could be the best thing since sliced bread…and we’ll all be grateful for your ingenuity. But not if you repel us all first. Then we’ll just ignore you – mean girls style.

Your Sense Of Humor

Fact: Shit will go wrong all the time on an island. Plans are awesome to make, but equally as awesome? Rolling with it – with a smile – when nothing works out as planned.

You might make a grand To Do list for your free day. Visions of supreme efficiency dancing in your head. Today’s your day and you can feel it! You will tick everything off the list before lunch and be sipping a mai tai before happy hour even begins. Or not.

Some days, no matter how much you plan, you just won’t get anything accomplished. Not for lack of trying, either. Maybe the government office you need to visit is unexpectedly closed (there are a lot of unique holidays in the Caribbean…often in the middle of the week). Perhaps you brought the wrong paperwork, so you’ll have to come again another day. Or it is lunchtime and everything is closing…too bad if you’re still in line. Or your island car breaks down. There are a gazillion things that can – and will – quickly derail your motivated plans.


It’s what you do next that seals your fate. As noted above, kicking or screaming or general frustration will do you no good. Instead, you just need to laugh about the absurdity and move on. Preferably to a beach. Or a bar. Or a beach bar. Even better.

I’ve had supremely frustrating days on this rock. Days where I felt like screaming to the heavens or punching something (or someone). All because I was trying to do something that seemed relatively simple. Yet it all went horribly wrong. And it was damn hot, turning me into a sweaty, pissed off mess. Heat and frustration do not mix (and your hair looks frightful). But I quickly learned that getting upset does absolutely no good. Nobody else cares, and the only person’s day I ever ruined was my own.

It is a legitimate truth on a rock that some days were just meant to be beach days. Or pool days. Or cocktail-into-oblivion days (stay away from bodies of water on those days…safety first). And the best part? It is totally OK to have a day like that every now and again. In fact, the alternative is probably to keel over from a stress-induced heart attack. And who wants to ruin their day in that way? So actually, those “do nothing responsible” days are exactly what the doctor would order.

The bottom line? Just. Keep. Laughing. No matter what.

Ok…so I realize this might not be the packing tips you were hoping for. But trust me…these are more valuable to bring with you than any swimwear or costume essentials. The best part? These take up zero space and don’t weigh a thing. Huzzah! You’ll still have plenty of space for those bikinis and cute cover-ups. Maybe even a few pairs of high heels if that’s your thing. But if I were you, I’d leave the ski goggles behind. If you need any, you can just borrow mine.

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