all your senses are on full blast when you’re in the middle of the ocean…
WHO: Duncan Molesworth
WHERE: St. Thomas, Virgin Islands
WHAT: Business Owner, Boat Captain
In part 1, we learned about the leading Jeep adventure company in the Virgin Islands, IslandBuddy. For part 2, we take a deep dive into IslandBuddy’s founder, Duncan. A business owner and boat captain, read on to find a glimpse of what island life is like, the intricacies of being a charter boat captain, and feel what it’s like to truly trust your friends when alone on a small sailboat for seven days.
Me: Tell me about island life.
Duncan: It can be extremely exhausting and extremely relaxing. It’s all sorts of extremes sometimes. Depending on what you’re looking for, it can either be very enjoyable or very frustrating. When you’re looking for a day off, it’s not a terrible thing to turn your phone off for the day. No one is going to complain that they can’t reach you. And that is very refreshing because I think we’re always raised to be on time, to be punctual, things like that, so we put a lot of stress on ourselves to always be around to answer the phone. That stresses you out and wears you down even if you don’t know it. So one thing I learned is island time, which everyone talks about, but it’s a real thing.
Me: What is “island time”?
Duncan: It goes deeper than just “you can’t find things”. Sometimes the power goes out. Sometimes there are days where you just can’t get ahold of people, but what you start to realize is, maybe these people needed time away from their phones to catch up on work or catch up on their mental health. And when you do finally get around to talking to them, there’s no hard feelings or arguments. It’s hard to articulate but it’s definitely what you make it. You can be who you want to be and you don’t owe anyone an explanation. You’re able to stop for a moment and just take some time to enjoy the place.
clear water, white sand beaches, swimming with sea turtles.
Me: You’re a boat captain, among other things. What’s that like? How hard is it?
Duncan: When I was in high school, we lived on a lake and we had a pontoon boat. So that’s where I got my training wheels, on the boat almost daily in the summer for years. Then I moved down to the Virgin Islands and I was working at a restaurant on a hill looking down at all these boats and all I wanted to do was be on the water. So that’s when I decided to invest time and money into becoming a boat captain, so I can not only be on the water but get paid to do it. I signed up for classes, got all sorts of certifications, and after almost a decade of putting in hard work, on the lake and in the Caribbean, I became a licensed captain. Then I just started reaching out to help out in any way. Then that turned into picking up captain shifts. It was a lengthy process but nothing impossible.
Me: What kind of boats do you captain?
Duncan: I’ve gotten a lot of unique experiences learning different vessels. I’ve captained 26-foot center consoles with outboards, to larger in-board mini-yachts, multiple 300-HP engine center consoles, and I even started out running a small shuttle from beach to beach in a 14-foot zodiac inflatable. It’s been a lot of fun.
Me: Describe to me a normal day in the life of boat captain Dunc.
Duncan: Wake up, eat a little breakfast. I try to take the mornings slow and to myself. Get to the boat about an hour early so I’m not in a rush. Guests show up right at the dock, go over safety precautions and equipment, and then we go over a map and see where they want to go. I want them to have a unique trip each time they’re with me. So set out with a loose plan and from there, after each stop, we reconvene to check in on the plan. We spend a lot of time snorkeling, beautiful clear water, white sand beaches, swimming with sea turtles. Then we’ll hit lunch, maybe find a place to tie some pool noodles and kick back with cocktails, beers, and wine down before heading back to the dock to end the day.
Me: Clean the boat and done?
Duncan: Clean the boat, gas up if we need to, then set the boat up for the charter the next day.
Me: Not a bad day.
Duncan: Not bad. We work from 9 to 4 and when we’re done, we still have plenty of sunlight left. I can go run errands and get other projects done, or take my dinghy to St. John to catch happy hour.
Me: Have you ever had any scary situations on a boat? Any guests that have just been terrible?
Duncan: Yes and yes. The pandemic has really changed travel. A lot of people are coming down for the first time, which is good, but it seems like there’s a lot of people that don’t know anything about this place, don’t understand how to stay safe in the water. Like maybe they’ve never swam in the ocean before, and they’re going on boat trips. So lately we’ve been more than a captain. We’re lifeguards, bartenders, snorkel and swimming instructors, which is kind of what a boat captain is anyway, but it’s just a little more labor intensive lately. And it requires a lot of patience.
Something scary that happened? I was leaving the dock on St. Thomas. I put the boat in reverse and backed out of the slip, then put the boat in forward but it kept going backward. So I had to cut [the engines] and I’m dead in the water. Turns out there was a broken throttle cable. And thankfully there were no guests on board, but it had me startled. When your boat is stuck in gear in tight quarters near other beautiful, beautiful boats, it’s definitely a nerve-racking situation. But I was able to get it back in the slip, all untouched and everything in one piece.
they’ve got your life in their hands.
Me: You sometimes find yourself on adventures with connections you know. Tell me about some other cool things you’ve done.
Duncan: I did a delivery from St. Thomas to Ft. Lauderdale on a mono-hull sailboat, and that was a very sobering experience. It makes you realize how small you are on this giant world. We did eleven hundred miles in 7 days all under sail, 24 hours a day. We had planned our route using the tides and the weather and just tried to enjoy the ride. I got to see a sunrise and a sunset every single day.
Me: And people don’t really do that, right? Stop and watch the sunset. You just kind of go about your day and the sun rises or the sun sets.
Duncan: Right right. When you’re out sailing, you’re completely in tune with nature. You’re paying attention to what the water is doing and what the wind is doing because each little change affects your sailing, your speed, your course, so when sunrise and sunset came each day, it took the main stage. When I say we watched it every single day, we paid attention to every single second of its performance. They were very sobering and very, very beautiful. Each day it was different, with different clouds and conditions and colors. And to be with two other humans for a week straight on a 40-foot sailboat out in the middle of the ocean, you kind of develop a bond with those guys. They’re the only interaction you have and if something were to happen, they’ve got your life in their hands.
Me: So you’re with these people 24/7 and the boats not huge, right? You probably can’t go 30 minutes without bumping into someone I imagine.
Duncan: We were so close quarters that if you coughed, the other guy would hear you and wake up. And all of your senses are on full blast cause you’re out in the middle of the ocean and there’s this sense of survival going on. You’re one bad turn from being stranded out at sea. So you’re very alert, there’s tons of coffee, trying to stay awake. And even when you’re resting, you can’t, because you’re so nervous.
Me: What’s that like? Entrusting these people that you’re with when you do try to sit down to rest?
Duncan: I took the delivery because of who the captain was. My buddy I was with does 5-6 of these a year, so when he asked me to go along, I said yes, knowing that he had thousands and thousands of miles under his belt. I knew it was another walk in the park for him. Because of that I felt safe enough to go on this adventure. That allowed me that piece of mind knowing he was in control and I was just along for the ride.
(Have the time? Check out 16 Days at Sea on YouTube, or read about it here)
it’s just God’s country man.
Me: Where all have you been?
Duncan: Hawaii, St. Martin, Puerto Rico, Costa Rica, El Salvador, Grand Cayman, Aruba, Key West. I’ve been to the Smoky’s, the Blue Ridge Parkway, really the whole Appalachian chain. I’ve been to several national parks, and my favorite is probably Glacier.
Me: Why?
Duncan: I think Montana is just a whole different, it’s just God’s country man. It’s just landscape after landscape, untouched earth. And the topography is insane, and the sky is insane, and it’s all untouched and undeveloped.
Me: Where do you find inspiration? What keeps you inspired to keep saying yes to adventures?
Duncan: You don’t know what’s going to happen, and there’s a chance you’re going to learn something along the way. And the thing I enjoy the most in life is seeing new places, meeting new people, and learning new things.
Me: What’s next for you?
Duncan: I’m developing a small property I own here in St. Thomas into small luxury cottages with a large central common area where I can host travelers from all over the world, give them a beautiful place to stay. So building that and bringing people together is what’s next, using the view, the breeze, the tropical climate as the focus, providing a place to host and gather while enjoying the landscape and everything that it has to offer. The fruit trees, the lizards, things like that. I’m really looking forward to it.
Give Duncan a shout on Instagram at @duncan_nm, and read part 1 of his story here.
And as always, stay tuned to this space for more of the best stories of adventure.
Live Lost. Find it on the way.
