Capt. Derek Watkins
One of my favorite quotes of all time comes from JRR Tolkien’s book, The Fellowship of the Rings, where Gandalf said to Frodo… “All we have to decide is what to do with the time that is given us.”
Born and raised 20 miles north of Boston in Reading, Massachusetts, I loved the outdoors and playing any and all sports. My summers were spent in the White Mountains of New Hampshire until sports took over my life, along with my family’s. After graduating from Reading Memorial High School, I decided to pursue my love for athletics and attended East Stroudsburg University in the Pocono Mountains of Pennsylvania to play college football.
A few years later, while living in Wells, Maine, I decided to follow in my grandfather’s footsteps and become a bartender. That decision changed the course of my life forever. For the next 25ish years, I used the bartending profession to fuel my passion for traveling and adventure. I also learned as many trades as I could: carpenter, ski and snowboard tech, Alaskan fisherman, paint salesman, tour manager, and owner and operator of my own and muscular therapy business. I called Boston, LA, Sitka Alaska, Aspen Colorado, Squaw Valley/North Lake Tahoe, New York City, and St John, USVI my home. Of course, my life was not all work and no play. I found time to fall in love with the great outdoors all over again and became an avid backpacker, snowboarder, mountain biker, and traveler. I visited India, Nepal, Central America, Eastern and Western Europe, along with many states in the USA.
In 2003, friends showed me photos of Maho Bay on St John in the USVI. I had never heard of St John, or USVI in fact. However, the beauty I saw in those photos never left my thoughts. I almost visited several times over the years, but it never worked out. Then, one day in NYC, I decided it was time to make a change. So, I bought a one-way ticket to St John. On the first day after I arrived on St John, I found a bartending job. On my third day, I was invited to go sailing for the first time ever. That day was literally life changing. From the second I stepped on to the sailboat I knew I wanted to learn how to sail and become a captain. Now, I hold a USCG 100 Ton Masters License with Sailing Endorsements, CPR and First Aid certificates, as well as my STCW-95. Going on my seventh year here in the USVI, I am ready to accommodate your itinerary in a safe and knowledgeable way. My goal is to make sure your trip is a beautiful, lifelong memory; because…this is what you’ve decided to do with your time. Welcome Aboard!

Haddiyyah A.K.
If you are looking for constant laughter and someone to put a smile on your face, then Chef Haddiyyah is your girl. Her friends are quick to point her out as the comedian of the group. She says, “if I can make someone else smile, that makes me smile.” She is also a person that likes to uplift and empower others. She loves this industry because she gets to share her favorite thing with the guests, which is a day on the water. She says, “there are so many unique things to explore, to be able to share those experiences with others is great!”
Chef Haddiyyah had been in the kitchen since 7 years old playing as a sou chef to her mother who was a soul food chef as she was growing up. When asked to describe her food she says “it’s soul food infusions”. Haddiyyah is a wonderful leader but is always willing to learn more. She is a true team player and has no problem going the extra mile. Born in Philadelphia, Pennsylvania she has lived in multiple places where she learned flexibility and in turn it made her extremely well-rounded and able to adapt to any environment.
Eventually, Haddiyyah found her way to St Thomas, USVI. Though her degrees are in communication, international relations, and sociology, her love for the ocean and the yachting industry grew quickly. Through hard work and dedication, she earned her 100-ton USCG Master’s License and STCW. In 2022, she became a graduate of the Virgin Islands Professional Charter Association marine apprenticeship-intensive captain’s training program.One of her goals is to be able to extend a helping hand; providing resources to the next generation of underrepresented communities and to help goal-oriented individuals become successful (preferably in the boating industry).