When people ask me, "How did you end up down in the Caribbean?" my surface-level answer has often been, "I was in a relationship with a guy who grew up down there." But the real answer is much more entertaining.

I always loved the song, "Brandy, You're a Fine Girl" -- I always wanted to be the sailor girl, or just to-be known in the context of that song.

I wanted to be identified as a woman who's no stranger to the sea.

Sailing a transatlantic passage, at one point, was a bucket list item for me (...and one bout on a rinky-dinky 46' monohull to the Spanish Virgin Islands during the Christmas winds dissolved that desire. That desire, mixed with other adrenaline-filled liquids, dripped right out of my pores during those 36 hours of hell.)

"How Did You End Up As A Term Charter Yacht Chef In The Caribbean?" The Real Story

13 years old, summer break, going through my transition into who I wanted to identify myself as in the world, my mom would rent me different movies to watch from the library. There was this one movie about some Englishmen who chose to be an ambassador on a Caribbean island. It shows all of the frivolity of social dynamics, the hoops to jump through, but it also showed them on boats coming up mangrove nurseries. It showed white birds nesting through the low-hanging trees with elaborate plumage. This Caribbean movie showed how everyone was sun-baked; everyone had a glistening sheen of sweat in every scene. Cultures clashing, mixing, mingling between the ex-pats and the West Indians locals with their accents I could only identify as "Jamaican" at the time. Seeing the frenzy of different people from all walks of life, all in one tiny island, something about it lit my heart up. There was adventure, beauty, mild chaos, culture, sweat, absolute paradise. I made a silent agreement with myself behind that coffee table, cheese quesadilla in hand that day, that I would live on an island at some point in my life.

"I'm going to live on an island in the Caribbean one day." 

I went through a phase that teenage summer with a mild obsession with Caribbean culture. I bought every Bob Marley CD I could get my hands on from the local CD Baby Buy.Sell.Trade. store off 183.  I attempted to learn how to talk and type (on AOL Instant Messenger) as though I were a Rastafarian, putting Away Messages like, "Everything Irie." 

I studied Ras Tafari, the roots of Selassie I, and what Bob Marley believed.  I'd sunbathe outside on the patio and blast the Natural Mystic album. I made macrame hemp jewelry all summer, ready to sell it at the next Bob Marley Festival at Auditorium Shores.

I quickly realized I couldn't pull off keeping up a Rasta dialect in real life, but I wore my Bob Marley shirts on a rotation. I attempted to order a Dreadlock kit to dread my hair myself. My mom wouldn't buy it for me, so I asked one of my neighbors if she would buy me the kit. She did. My mom found out, and explicitly told me she would shave my entire head if I dreaded my hair (I firmly believe she would), so the kit was returned. 

My reggae phase blended into other things, but that life goal of living on an island in the Caribbean never faded.

When I met the family of my future first-husband (yesterday would have been our 10-year anniversary, how crazy is that) and learned of their upbringing in the between Austin and the Caribbean, something resonated in me.

The Journey Of The Young Sagittarius Woman

In one of my favorite fun reads, Sextrology, there's a section describing how a pattern of Sagittarius women and their life paths is they'll often choose their first mate to be someone they can pair their lives with to help them "level up" into a different social class or different state of experience in the world. The young sagittarius woman often marries young. Usually, those relationships don't end up being long-lived; but they help the young Sagittarius catch up their external life experiences to match the Young Sag's advanced internal world.

I couldn't agree more.

Moving Down To The U.S. Virgin Islands As A Young Bride

Moving down to their islands as a young bride, expecting to live out of my British ambassador movie lifestyle, my reality ended up being quite different.

But it got me there.

I got my footing in acclimating to the chaotic Caribbean and island-life culture. Returning down to the Virgin Islands post-divorce, that marriage and living in his family's orbit had given me a foundational base to build from, and I'm so thankful for that. 

I lived down in the Caribbean from 19 to 23 consistently. I conquered several life goals: 

• living on an island

• learning how to be competent on a boat and on the water. My dad always took the reigns on our weekly lake outings growing up by Lake Travis in Austin, but I mostly learned the skill of get-out-of-the-way.

My Sailing Crew Career

My sailing career brought me through being a third mate, to second mate, to first mate on a 65' Sloop-rigged Ferro-cement monohull where we'd take our guests out snorkeling and then another group of guests for a sunset cruise, cooking aboard and feeding 35 people per shift. It was a day charter operation that stayed within the U.S. Virgin Islands (RIP New Horizons! We loved you and drinking your booze!) 

Post-divorce, the only job I was interested in returning for would be a private chef / first mate job aboard term charter sailboats in the British Virgin Islands. I put that intention out there, met a woman who knew a woman, had 48 hours and a job interview later, I landed my next position as a term-charter yacht chef in the BVI.

“Did You Go To Culinary School?” What It Really Takes To Be A Term Charter Yacht Chef + First Mate

I cooked on term charter catamaran (two hulled) sailboats for two years.

The next question I usually get at this point was, “Did you go to culinary school?” and the answer to that? Definitely not. If you’ve ever stepped foot on a 40-60 foot sailboat of any kind, you’ll quickly realize the “kitchen” in a sailboat is much more like cooking in an RV camper. Many of these term charter boats initially attempted to fly down stateside chefs with proper culinary educations, but being presented with a mini-fridge (or two if they’re lucky), a two-burner stove, an inconsistent oven, and the a kitchen that’s rocking and pitching side-to-side up to 35 degrees at a time, OH! Did I mention? You have to provision, prepare, and store eight days of food for up to eight people at a time? These classically trained chefs term-charter yachting careers are typically VERY short lived.

What you need is someone with docking, mooring, and anchoring experience, who’s scrappy as hell, and can get the job done.

I can get the job done. I can cook a mean grilled cheese, and crank a winch so efficiently you might get an erection. I’m just saying.

The most distinguishing trait of the best of the best yacht chefs I know in the charter yacht world is resilience.

The ability to roll with the punches, and quickly pivot when your freezer goes out and you’ve got to re-arrange your entire menu plan before the meat thaws and spoils. People like Jayde Cousin, my favorite boat babe, Laura (pictured above, she’s the one who trained me as a mate back in the day!!)

Those who can go from a lunch stir fry beef-with-broccoli, hearing their captain’s knock above them as he pulls into an anchorage, haul ass up top, go grab that mooring ball, and run back to your skillet before your broccoli overcooks — these are the badasses of the charter fleet world.

Creativity, presentation, and being elastic as hell are your #1 assets for thriving as a term charter yacht chef.

Providing fantastic customer service in the midst of uncommunicated food allergies, that one person in the group is lactose-intolerant or gluten free, or half of your charter guests are jewish and Paleo, and their friend who DIDN’T fill out their preference sheet is secretly pregnant, and all she wants is bread, potatoes and cereal. #truestory

You have to have nerves of steel to be sail-trimmer, dish-washer, cook, janitor, bed-maker, and tour guide with a roulette of 8 different humans for 8 days at a time.

The Life Of Being A Term-Charter Sailboat Chef In The Caribbean

I joined sailing flotillas to Puerto Rico to hull out. I sailed to the Spanish Virgin Islands. I helped friends run boat deliveries from St. Maarten back to the U.S. Virgin Islands.  The last delivery we covered 350 nautical miles, sailing our way up of the Eastern Caribbean islands, delivering a 62' Fontaine Pajot catamaran sailboat from Fort De France on Martinique to its new fleet in St. Thomas, U.S. Virgin Islands.

I made some of my closest lifelong friends working on term charter sailboats. I have some my best, most outrageous stories from this time of sun, sweat, and salty water in the Caribbean. I have scars from rum-fueled nights of debauchery and horrific sailing trips gone awry and close calls. I’ve freedived (freedove?) with turtles and been an arms reach of sharks. I’ve gone tubing butt-ass naked in broad daylight in the most popular anchorages in the BVI. I’ve locked eyes with my captain while falling into what I thought would be my death being prop chopped. I probably have premature sun damage and sunspots. I definitely laugh lines, smile lines, and premature crows feet in the corners of my eyes from smiling and laughing so hard during this chapter of my life, too.

I lived out one expression of being an ambassador on a Caribbean island. I found my own perfect mess of chaos, adventure, sweat, and family. And I'd do it all again, in a heartbeat.

If you’d love to learn more about this world, check out my travel blog, Travels With Shelby — Where I chronicled a daily retelling of the biggest boat delivery I did from Martinique to St. Thomas, USVI!