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By popular demand, here is the second installment of my interview series: Women Making Waves – or as I affectionally like to call it: “Badass Female Captain Interviews”. Thank you so much for the overwhelming response after the very first interview with Captain Katie. This week I am featuring one of my good friends from the Virgin Islands: Captain Molly.

I met Molly four years ago when I was working in the Virgin Islands. She was freelancing on many different boats. She would always sub for us and eventually worked with us consistently on Kekoa (the boat I worked for). Working with Molly was incredible – while some of us would be burnt out and tired of doing the same thing everyday, Molly would run circles around us scrubbing coolers, reorganizing t-shirts, doing inventories – I remember sometimes we would have to ask her to stop so we felt less guilty about taking a break! Molly and I took our captain’s course together, and she has been killing it ever since. I was so happy when Molly agreed to chat with me for this interview because she is a total badass, and one of the most hardworking individuals I’ve ever met. Having never stepped foot on a sailboat in 2009, she is living proof that with a lot of hard work and determination you can be anything you want to be!

1. Where are you from?

I grew up just outside of Kansas City, Missouri (Go Royals!)

2. When and where did you first learn about boating? 

I moved to the VI from the largest man-made lake in the United States. There, I enjoyed plenty of cocktails while lounging on boats, but all of my actual boating experience came from the moment I stepped foot in the Virgin Islands. That was October of 2009.

I had never even been on a sailboat until I moved here. Once I realized that I could make a living working on boats, I made large efforts to learn.

After I worked my first season on St Thomas on a powerboat, I knew I wanted to learn to sail. I moved to Maine for a short period of time to learn about sailing and what prepping a sailboat for a delivery entails. At the time I didn’t feel like I was learning as much as I thought. Looking back, my first year I gained a great deal of knowledge that I still use today. 

3. What events led you to seek a position working on a boat? 

When I first moved to the Virgin Islands, I fully intended to bartend. Honestly, I didn’t even know working on a boat was a job. I moved to St John during the slowest part of the year, and I was having a really hard time finding a bartending job. After chatting with a few locals, they suggested I try to find a job on a boat. As a newbie, it’s basically bartending, but on a boat! How fun! The first job I was offered was on a 65’ sloop on St Thomas. So I moved over to the big rock and started my new adventure! I still remember the first day feeling the boat heel over —feeling nervous and excited! 


Read: 11 Badass Facts About Girls Who Work on Boats

4. What is your current position, and work history?

I currently captain for Captain Nautica Powerboat Expeditions. We mostly to cater to cruise ship passengers doing the dreaded “3 hour tour” (insert Gilligans island theme song). We often make it over to St John and even to the British Virgin Islands. In the past I have had the best jobs EVER! I mostly worked as a freelance crew member. That means I got to work on MANY different boats, with MANY different captains and crew, going to MANY different destinations. I’m not kidding when I say it was the best job ever. I feel so lucky to have gotten to experience such a wide variety of boats. One day I would be working on a 50’ catamaran carrying 80 people for a booze cruise, the next day a 50’ Sea Ray doing luxury tours around the BVI, and maybe on a third day I’d be on a monohull sailboat giving snorkel tours at our favorite secluded stops. I even did some yacht work. I’ve been the chef/stew/deckhand on a few 90’ yachts – but I decided the white glove and linen tablecloth life is definitely not for me.

5. Describe an average workday in the life of Captain Molly.

I usually wake up before the sun rises. My report time for work is usually between 6-7 AM. I head the marina just a mile away from my house and begin the day. Grab all my paperwork and necessities from our office and on to the boat. We have a basic morning checklist that I go through which involves checking oil, bilge pumps, inspecting lines, hoses, batteries, intakes, etc. We drive 7 miles from our marina on the east end of St Thomas to the cruise ship dock on the south side. There, we pick up our passengers and head out to Buck Island, and island 3 miles to the south of St Thomas. Our guests snorkel twice and we serve small snacks, soda and water. We don’t serve any alcohol, which is a first for me, but I LOVE it. Our guests are actually interested in snorkeling – not just boozing!

Because we are power boat in the midst of 20 sailboats that also pick up cruise ship passengers, we are able to get places first, and fast, and snorkel twice. That is what sets us apart. We then head back to the dock and drop off the first set of passengers and pick up the next 20. On the busiest days we will do 3 trips. After we’ve dropped off the last crew, we head back 7 miles to the marina. This time straight upwind, where on the south side of St Thomas it usually blows 20-25kts all winter. That is definitely my least favorite part of the day. We have to fuel the boat every other day before hitting the marina. Once we are secure in the slip I turn off the batteries, grab the keys and I am done. That’s one of the perks of working on a small boat. There’s not room for two people to be cleaning and scrubbing, so the captain heads to turn in paperwork and usually chat with the boss lady. On a two trip day I’m usually home by 430. Some people think it’s comparable to the movie Groundhog’s Day, where a lot of our days look the same. To me, every day is always a little bit different and I’m not tired of it yet!

6. What’s the best part about working on a boat?

Hands down the best thing about working on a boat is the experiences I’ve had and the nature I have seen. Just last week I saw turtles eating a jellyfish! Amazing! I’ve seen whales breaching (my favorite time of the year!), dolphins jumping in the boat wake, sharks, stingrays. octopus, eels, lion fish, and more.

I’ve seen more islands than most people will see in a lifetime.

I’ve been to all the major US, British and Spanish Virgin Islands. All while GETTING PAID. My dad constantly asks when I’m going to move home and get a “real job,” but my response always goes somewhere along the lines of “ Why would I want to leave a job where I get paid to do things people pay thousands of dollars to do?” We also always have a pretty good tan, thats a pretty good perk. 



7. What are some of the struggles?

This might be more personal, I’ve never been great at saving money, but this industry is definitely feast or famine. Although we can basically work all year round, come September and October (hurricane season) money always seems to be a little too tight for comfort. In April you’ll find me splurging on new swim suits and gadgets, in October I’m eating ramen noodles. Along the same lines, our job doesn’t come with the typical benefits that one might find with a “normal job.” We are not on salary, so again, when we don’t work, we don’t make any money. No paid vacations. This also means no health insurance, no 401k, no dental plans. I can’t speak for other boat jobs outside of St Thomas, but there was only one boat here that offered any of those benefits, and it no longer does. Most boat jobs are not corporate positions, so it seems unsustainable for someone who is aging or on the verge of retirement. 

8. What’s the best job you’ve ever had on a boat? 

That’s a hard question! Mostly because I’ve had so many – that’s the best job: freelancing! 

There are some boats where I made the best money, some where I worked with best people, and some where it was just the best boat – and those are definitely not the same boats! Where I met Captain Liz, on Kekoa, will always be a boat that stands out in my mind. It wasn’t perfect, and it has its negatives just like every other job you’ve ever had, but the girls I worked with and the fun times we had on that boat made it pretty memorable. We were an all girl crew (with the occasional male owner making an appearance from time to time) working, and basically managing, a 50’ sailing catamaran. We did tours all over the British and US Virgin Islands. Half days, full days, sunsets, weddings, concerts, you name it. We all worked together on every project, and were constantly asking questions and forming nautical related discussions with one another. We had a captain who was obviously in charge, but she (either of them) would gladly volunteer to clean the head at the end of the day. There was never a ranking system. I loved that. We all hung out outside of work, spent holidays together, and I still talk to each of these girls frequently today. We made some lasting bonds, and I was even the last one in! Liz and I even took captains school together, and we definitely relied on one another to make it through those 3 weeks of intense work and studying. At the time, that was one boat and crew we were all proud to be a part of. 

9. What are some of your hobbies outside of work, and how (if in any way) has your job helped you to develop these interests?

I love anything on the water! Scuba diving, snorkeling, swimming, beaching, photography & videography — never leave home without the GoPro! In the past year I’ve taken up a lot of yoga. After 6 years of working on boats, being on my feet all day, I was looking for a good way to decompress my spine and just feel better in general. Working on boats is hard on your body. Yoga and especially aerial yoga is a non-intensive exercise that I can still motivate myself to do after a long day of work. It is a good way to let any stresses go and clear my mind too.  Now, when I don’t get a couple classes a week I notice how different my mind and body feel. So really, my job brought me to my new found love of yoga. The diving and snorkeling go hand in hand with my job. I have of love of the ocean! Im always wanting to discover and experience every part of it!

captain molly yoga

10. What’s the best advice you could give to people interested in getting a job in this field?

Don’t wait! It’s way easier than I ever thought to get a job in this industry, and its not for everyone. If it’s for you, you’ll know it. You’ll feel the passion and the joy that me and my friends do. I read this on a Facebook last night and it rung pretty true to me “ Vacations lie. Culture tells us to spend an entire year saving for a week to escape our life. We call it vacation. Vacations are meant to be new, they are meant to be fun, but they aren’t meant to be better than your real life. Life isn’t about the 50 vacations you’ll take while you’re on this planet. It’s about the 25,000 days between them. Stop creating a life that you need a vacation from. Instead, move to where you want to live, do what you want to do, start what you want to start and create the life you want today. This isn’t rehearsal people. This is YOUR life.” Dale Partridge.

11. Any advice for Female Captains Specifically? 

Wanting to become a captain in a  field mostly dominated by men, can be very intimidating. There were only two girls in my captains course, and there are somewhere around 10 female captains I can think of in the Virgin Islands on probably around 75 charter boats. Anybody can drive the boat from point A to point B right? The biggest nerve-wracking 5 minutes is docking. Personally, I dock our boat in a busy, busy port where at any given time there are 10 boats waiting for the dock space. When I first started I always felt the pressure of others watching me, something I don’t think that male captains feel as much. It’s probably not true, but at first I felt like people were watching, waiting for me to fail. I remember the first couple times my heart racing, and it always felt good to nail it. Now, it feels like anything else we do. So for those girls scared to try, keep in mind, that butterfly feeling will go away! We’ve all been there. Nobody’s perfect, we will all make mistakes. If you never try, you’ll never get that rewarding feeling of just nailing your docking, anchoring, whatever, whether anybody is watching or not. 

You can follow Molly’s adventures in the Virgin Islands on her instagram: @goodgollymsmollymarie.



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