There are picturesque sunsets, beach days, old towns and boat trips; there are cocktails and long naps; there’s not a worry in the world. Island life is simple, uncomplicated, and free from the materialistic things that are supposed to make you happy. Island life is the dream… Right??!
Well, kinda… Real island life - just like life anywhere in the world - comes with it’s own challenges that are not all insta-worthy! Most of you have been friends of mine for a long time, and know many of my stories from my past island life, so this week I thought I’d bring in some fresh stories from another island girl: My sister, Amy. Here’s our chat about island living, the life lessons that it teaches, and of course a little bit of fashion thrown in. Enjoy!
[KIM] Hey Amy, thanks so much for letting us into your past island life. First, can you tell my readers a bit about your history with the Caribbean and what turned you into an island girl?
[AMY] Hi Kimma, thanks for having me! It’s a pleasure to meet your island family. Hi, lovelies! Well, I first visited the Caribbean when I was only about 15 when my parents & I were visiting Kim and Justin. I rocked up to their tiny boat with the world's largest suitcase, which just about sunk their dinghy… And yup, they’ve never let me live that down. Ha! We cruised around St. Vincent and the Grenadines that trip and had an amazing time despite my epic seasickness! I visited Kim again a couple of years later when she was living in St Maarten and I think from that trip on, the island lifestyle had its grip on me. Although I did go home to continue university after that trip, it only took a few months for me to realize that the travel bug had bitten and perhaps studying wasn’t for me… In 2006, at the ripe age of 21 I set off on a round-the-world ticket: first stop LA, NYC then to meet Kim in the southern Caribbean island of Grenada. I joined them to “help” sail back up to St Maarten after Hurricane season but hilariously, I was very little help. I was chronically seasick for days at sea and was given the nickname: The Phantom Puker. It was truly the worst! Even 3-year-old Maya looked at me like I was ridiculous curled up around a bucket in the cockpit of their 43ft S/Y Sahara. Delirious and exhausted, I remember kissing the ground when we finally made it to St Maarten: then, most likely headed straight to the nearest beach bar for a strong Vodka & Ting 😅
Now, you are probably thinking that being so sick on a boat, would be enough to have my feet planted solidly to dry ground for ever… And you’d be strangely wrong! 😜 Within a few weeks, I had my heart set on a super yacht job and started doing all the things necessary to become a stewardess:
Update resume ✅
Invest in a plain white polo shirt ✅
Suck up my pride and prepare to clean things... really well...
And, attend every single wild crew party there was during January in St Maarten ✅ ✅ ✅
I got my first job on M/Y Relentless back on January 27, 2007. I was very young, very inexperienced, and very naive, but also incredibly hard-working and grateful for the adventure to come! Kim tearfully signed me off her boat crew and waved me goodbye as the draw bridge opened in Simpson Bay. And in the words of one of my all-time favorite children’s books, I was off to find the shimmering ice and coral caves, and shooting stars, and enormous waves!
I was a stewardess on many large super yachts for the next 6 years and traveled to many amazing islands. I explored the Caribbean, Bahamas, East Coast of USA, Europe, and the Mediterranean, as well as Central America. I cured my epic seasickness with pure stubbornness and went on to cross the Atlantic Ocean 3 times. While the job itself was challenging, and of course, I missed my family, I had an absolute BLAST!
[KIM] I know you worked hard on the boats and often had paying charter guests onboard for weeks, meaning you had no downtime. But, did you ever get to explore the amazing island locations that you visited? Or were you too busy working?
[AMY] Yeah, that was a bit tough sometimes. There were definitely some incredible locations that we stopped at and I only saw the shore through the stewardess pantry window, whilst hand washing fine crystal wine glasses 😜 but we did also get plenty of downtime between charters.
Generally, we picked up and dropped off guests at major ports, because they have an airport and those ports would be our “home base”. In the Caribbean, that was St. Maarten or St. Thomas. In the Bahamas, Nassau. In Europe, most often it was Mallorca. From there we would work regular hours and have the weekends free to roam. Being young and full of energy, I would often take weekends as an excuse to get away from the boat for a couple of days. To refresh, get away from any crew drama, and sleep in a bed that was bigger than a single bunk (and didn’t rock!). One of my favorite memories was a trip that I took with my friend Claire. On a whim we found cheap tickets from St Maarten to Panama and jumped at the opportunity to take some extra time off. We had been working really hard, both had boyfriend issues and just needed to get away. From Panama City, we hopped on a tiny plane that took us to the city/archipelago of Bocas del Toro. There are three main islands in Bocas Del Toro: The main island, Isla Colon
; Isla Bastimentos
, which is one of the largest islands in Panamá.
We stayed on Isla Colon but spent a week exploring the islands via paddle board, doing yoga, learning to surf (or trying) and hanging out at the beach. It was pure magic! Like many of my favorite island locations, Bocas really is a melting pot of mainland Panama culture and Caribbean vibe. Do you remember that vintage WIW photo of me in one of your original tunic dresses sipping the water from a coconut? That was from this trip!
We took a bus to Bocas del Drago, then a $1 boat ride to the famous Playa Estrella (Starfish Beach) and as soon as the boat stopped in shallow waters, we looked around in amazement at the clear turquoise water with what seemed like hundreds of starfish chilling on the white sand ocean floor. This trip was back in 2011 and as an original West Indies Wear model who had a suitcase full of cotton sarongs and tunics at all times, I was always looking for photo ops.
[KIM] Although you traveled to loads of tropical islands, you weren’t truly a full-time island girl until you left the boats right? Would you be up for telling Our Island Family about your post-superyacht island life, next week?
[AMY] I’d love to! After about 6 years of yachting, I decided I was ready to move onto dry land and stop moving around so much. I wasn’t quite ready to move home to Australia and get a 9-5 but I was ready to live in a house and have a bit more stability in my life. I didn’t really know what I wanted to do, until I was approached by a charter guest who owned a Caribbean island (yes, you heard me right… He owned the entire island) off the coast of Honduras. He was looking for an island Manager and thought I might be a good fit! I jumped at the opportunity and spent the next 5 years truly living the island life! I am excited to tell you about that next week.
[KIM] Great! Ok, one last question. What do you miss the most about being an island girl?
[AMY] Ha! Well, first of all… I don’t think you ever truly lose the essence of being an island girl and I really do think that you continue to carry the many lessons throughout your life. But, if there was a “thing” that I missed, it would probably be beach bars! Hahaha I know, I know, typical Amy. But there’s nowhere quite like the Caribbean when it comes to drinking iced cold beers with your feet in the sand. Live music is playing, there’s a smile on everyone’s face, laughter in the air, and the chill-factor is at an all-time high! That’s what I miss the most 😜 I can’t wait to share some stories from my time in Islas de la Bahia next week, island girls! Thanks for reading xx
[KIM] Thanks bub. This week, island girls, it’s my absolute pleasure to bring to you a dress that was inspired by my island girl sister… The Amy Dress. As you may already know, LINEN Is a new obsession for me and this gorgeous linen dress does not disappoint! Linen enhances breathability when you’re hot, locks in heat when you're cool, and keeps you just the right amount of comfy as you go through your day… Get excited, island girls! This week's launch of the Amy Dress comes with a FREE Gift valued at $69 but only while stocks last. Stay tuned to your inbox so you don’t miss the boat! 🚣♀️
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