Vessels of Freedom

Boats, vessels of freedom, harbors of healing… lyrics by Kenny Chesney

About a year and a half ago, we sailed on a crewed charter in the BVI’s. It was our second sail in the BVI’s, but by far the best. One of the things that made this such an incredible trip was the captain of our Lagoon 440 – the Red Stiletto. We were a bit of a rowdy crowd of 6 – we thought, but he had us sized up after our initial introduction and really tailored the trip to match our personalities and interests. By the end of the trip we felt that we’d won the captain lottery…


Darrel Hearne was his name and we could tell immediately by his wonderful accent that he hailed from somewhere other than where we were. As the week went on, we learned a little about his story and how he had made his way to the BVI’s. We recently contacted him to ask if we could interview him for our “Making Your Tropical Obsession Your Profession” series, and this is what we found out.

Give us a little background on what you did pre-BVI’s.
Well, I was in a very similar line of work before I came here – I was an accountant living 500 miles from the nearest ocean, so I guess it was sort of a natural progression for me.  Ok, maybe not.  I grew up in Johannesburg, South Africa, which lies in the center of the country and nowhere near an ocean.  My family were not boaters at all … in fact, up until the day that I quit my job and went to sailing school, I had never actually set foot on a sailboat in my life.  I did the usual thing … finished school, studied, had a proper job and wore the suit and tie of shame.  I did the daily commute to my office, where I lived behind a computer and did mundane things.  Thing is, I couldn’t see myself being an office lemming for the rest of my life.  It just wasn’t me.  I’m not really sure where the idea of moving to the Caribbean and becoming a sailor came from, but somehow it took root, and was something that I talked about for years.  One day, when I was 33, I realized that if I didn’t go then, then in a few years time making sweeping life changes like that would be so much harder, and it would be too late.  So I quit my job and went to sailing school, got on a plane and flew to the islands.  Easy as that.

What brought you to the BVI’s? How long have you been there?
It was a Boeing that brought me here.  747-700, I think.  Ah – you mean for what reason?  Well, I wanted to come to the Caribbean to develop a career as a sailor.  I actually didn’t do much research into the BVI’s before I came here – more like I closed my eyes and pointed randomly at a map of the Caribbean, and said ‘Hmmm – BVI’s.  That sounds interesting’.  Actually, I had heard that there were a lot of boats here, which was good enough for me.  I came over here to get a feel for it, and to finish my dive master course, and ended up never leaving.  It’s been six years now, and I do love it here.

What is your current position?
I have moved over to the dark side, and currently work on a power boat.  Yes, I know.  I sold out.  I spent five years on sailboats, but the career progression tends to be to bigger boats … which means, at some stage, power boats, especially if you’re a single guy – sailboats tend to employ crew couples.  Actually, she’s a beautiful boat, and I do enjoy her very much.  She’s a 74-foot Horizon called Viaggio, that runs term charters for a company called Virgin Traders (isn’t that a great name?) out of Nanny Cay.  It’s an interesting boat to run, because she’s big enough to have the big boat feel and systems, but small enough that we only run three crew, and I get to do all the mechanical maintenance and repairs, which is fun, and invaluable experience.  She’s also a very, very pretty boat, so that’s always good for meeting girls at bars.  ‘What do I do?  Well, I captain that boat over there…’ (points to the cool boat that everyone notices).  ‘Really?’, she says, her eyes widening with interest as she sidles closer ‘Tell me more…’.  Ah, it is an interesting life I lead.

 photo: SailDiveBVI

What do you like better about what you do and where you live now?
You know, I try to explain my life to old friends from back home, but it’s just too much of a gap to be able to put into words.  The whole lifestyle here is just so different.  I grew up in a very conservative community, and I’ve found that I’ve needed to re-evaluate all of my pre-conceived ideas and values, living here.  It really is an alternative reality.  Don’t get me wrong – at the end of the day, my job is just a job, and people here are just people.  I think the thing I like most here is that I’ve been exposed to so much.  I meet so many people from so many different walks of life… get to live their lives a week at a time.  I’ve done charters with porn stars and swingers and captains of industry and even a US assistant attorney-general.  It really opens your eyes and shows you how vast and varied this world is, and how little we actually know.  Well, that, and it’s perfectly acceptable to go to a bar and drink a beer or two at ten in the morning.  And of course there’s all those girls in bikinis.  I remember feeling, back when I used to live behind my computer in my little office, that I was the only crazy one amongst all the sane responsible people.  Coming here, to me, has felt like I’ve finally come home.

What other interests do you have?
Hmm.  Interests.  Let’s see now … there must be something … hmm.  I will say that diversity in social activities and options on island is sadly lacking.  It’s a small island, and the culture is very much a hanging-out-in-bars culture.  You’re bound to meet the same people in the same bars, night after night.  Add that to the fact that as a charter captain, you’re off island for half of your time, and have to put your social life on hold for that time, and it tends to constrict your recreational options.  I do some photography, which I enjoy, and I absolutely love kiteboarding, so when the wind is blowing and I’m not working, that’s usually what I’m doing.  Oh, and playing with my daughter, of course.  She’s two, and a little hooligan sunbeam.  So that’s fun. She’s my happy place.

What advice do you have for someone that really wants to make a change in their profession and/or location?
I remember when I was leaving my company back in South Africa, people would hear about what I was doing and where I was going, and tell me how brave they thought I was.  and I always thought ‘Wow – really?  I’m going sailing in the Caribbean – you’re the one who’s going to be stuck behind that desk for the next twenty years.  Who’s the brave one?’.  I would say, if you really want to do it, then just do it.  Be warned, though – it’s not always the idyllic dream that everyone thinks it is.  I mean, it’s beautiful down here, and I have a great job and get to sail the islands for a living.  At the end of the day, though, it’s just a job.  And there are aspects of it that you are not going to like.  Once you get past the scenery, real life down here is much the same as real life elsewhere.  I would say come and try it out and spend some time here first.  Chat to some of the people who have been here a long time.  There’s a reason that a lot of people come here for two or three years and then leave – it’s not for everyone.  There is a trade-off – what you gain in beaches and vistas, you lose in things like being able to actually have shops to buy nice things, or being able to get a Big Mac, or any of the other accoutrement’s of civilization.  I always tell people that they need to drink a beer, relax, and lower their expectations when they come here.  It’s the islands.  Things work differently here.  Not everyone can adjust to that.  If you can, though, then it absolutely is worth it.  If you plan to work on boats, get your qualification levels up to par, and try to add in some extras … a professional diving qualification is very useful, and there is a trend these days towards eco-tourism, so some skills and knowledge in that side of the business can be helpful.  Above all, pack light, and bring a spare liver.  You’re going to need it.  Sailing (ok, pushing the throttle forward) is only 5% of the job.  The real job is socialising and entertaining, which means taking people to lots of bars.  It’s a tough job, but I do it to the best of my ability.

Who were your favorite guests of all time – oh, never mind, we know the answer to that one :)
Ha.  Well now.  I have had a lot of fun charters.  And I do have a lot of stories to tell.  It’s funny – it’s the fun charters that are the hard ones.  The ones with the people who want to relax, and don’t really want to socialise are easy.  Tuck them into bed at 9:30 after a nice glass of warm milk.  It’s the ones where you get on with them like a house on fire and you stay up drinking with them and partying and being silly till three every night and then have to be up again at 7:30 the next morning to move the boat that kill you.  Still.  I shall tell you what I tell all my guests:  yes, of course you were my favourite charter of all time.

Anything else we should know?
Well, let’s see:  did you know that ‘Woman Hitler’ is an anagram for ‘mother-in-law’?  Makes you think, doesn’t it?  Other than that, not much to tell, really.  I will mention a fact that is well-known in the industry but little-known outside of it: working on boats is very tough on relationships.  Many many crew couples come here together and then split up – it’s being in close quarters 24/7, and never being alone that does it.  If you’re thinking about this kind of life as a couple, sit down and talk carefully about it.  Set some rules.  It’s very easy to lose sight of your focus down here.  It’s possible to get it right, and many couples do, and have been working in the industry for years.  You just need to be aware of the dangers.  That’s about it.  See you in the big blue yonder.

photo: SailDiveBVI

So there you have it; a very honest and candid look at living and working in the islands. If you are interested in a crewed powerboat charter, we’d highly recommend a week with Captain Darrel. Contact Virgin Traders to check on the availability of the Viaggio. You’ll feel as if you’d won the captain lottery too – oh, and don’t forget to bring that spare liver – you’ll need it!

Find other posts in the Making Your Tropical Obsession Your Profession Series


  1. Helene Hinely says:

    You should write a book. Not only a great man, sailor, but also a great writer. I love this story, so happy it was shared on Facebook. I so miss the Caribbean, moved to St.Croix in 2004, things did not work out, sad but true, wish I had tried harder to stay. It was a dream come true moving there, hope to vacation there someday.. Now living in Maryland, my hometown. Wishing you the best! Helene