Captain Derek Watkins

I was born and raised near Boston in a town called Reading, Massachusetts. I enjoyed spending time outdoors and playing various sports. During the summer, I used to go to a family campground near the White Mountains in New Hampshire. However, as I grew older, sports took over my life.

After graduating from Reading Memorial High School, I decided to pursue my passion for sports. I attended East Stroudsburg University in the Pocono Mountains of Pennsylvania, where I played college football. A few years later, I found myself living in Wells, Maine, and decided to pursue a different path. Following in my grandfather's footsteps, I became a bartender. This decision completely changed my life, allowing me to fund my love for traveling and adventure over the next 25 years.

During my time as a bartender, I not only mixed drinks but also acquired various other skills. I worked as a carpenter, a skis and snowboard technician, an Alaskan fisherman, a paint salesman, a tour manager, and even ran my own muscular therapy business. Throughout my journey, I called different places home including Boston, LA, Sitka Alaska, Aspen Colorado, Squaw Valley/North Lake Tahoe, New York City, and St. John in the US Virgin Islands.

However, my life wasn't all about work. I made sure to make time for fun and rekindled my love for the outdoors. I became passionate about activities like backpacking, snowboarding, mountain biking, and traveling. I had the opportunity to visit incredible places such as India, Nepal, Central America, and various states in the USA.

In 2003, I came across pictures of a place called Maho Bay on the island of St. John in the US Virgin Islands. Although I had knowledge that St. John or the US Virgin Islands existed, those photos left a lasting impression on me. I had the intention to visit several times over the years but it never worked out.

Eventually, while in New York City, I decided it was time for a change. I purchased a one-way ticket to St. John and on my very first day there, I secured a job as a bartender. However, it was on the third day that my life took a significant turn. I was invited to go sailing, an experience that would completely transform my life.

From the moment I set foot on that sailboat, I knew I wanted to learn how to sail and become a captain. Fast forward to today, and I have achieved that dream. I hold a USCG 100 Ton Masters License with Sailing Endorsements, along with CPR and First Aid certificates, and my STCW-95 qualification.

One quote that resonates deeply with me is from J.R.R. Tolkien's masterpiece, 'The Fellowship of the Ring.' Within the pages of this epic tale, Gandalf imparts his timeless wisdom to Frodo, saying, 'All we have to decide is what to do with the time that is given us.' These words have been a constant source of inspiration in my life, motivating me to seize each day and make the most of every moment."

Now, in my 8th year in the US Virgin Islands, I am ready to assist you in executing your dream trip in a safe and knowledgeable manner. My primary goal is to ensure that your journey becomes a beautiful and unforgettable memory. You have chosen how to spend your time, and I am here to welcome you aboard!


Chef Jody Oles

Chef Jody is a native Californian, but has loved chartering in the islands for the last 17 years. She holds a US Coast Guard Masters License, and is a PADI Scuba Instructor, as well as an accomplished charter chef. Her passion for beautiful food equals her passion for the ocean. Before moving to the islands, Jody was an educator for several zoos and aquariums on each coast. She fell in love with the Caribbean waters working as an Aquarist at Coral World Marine park in St Thomas. Her knowledge of marine life gives her guests an experience they won't forget! From the galley, her fresh breads, pastries, decadent desserts, and everything in between will present you with an array of goodies to tempt your taste buds. Her culinary style incorporates fresh local ingredients with culinary favorites for amazing meals that guests love. Her greatest pleasure is your smile of satisfaction!