Captain Jim
–
Captain Jim, Lisa and James
© Roaming Fin Media
Captain Jim at 28!
Man of the Sea
Growing up in Fairhaven Massachusetts, just across the bridge from the old whaling port of New Bedford, Jim dreamed of building his own boat one day and earning his living on the water. As a child, he would visit the New Bedford Whaling Museum as often as he could, absorbing the maritime history and culture of that lost era. It is only fitting, that the course he plotted throughout his young life would eventually lead him to Nantucket where he established his business and raised his family.
Want to learn more? Read our Q&A below⤵
Q&A with Captain Jim
How did you become interested in sailing? Did you come from a sailing family?
My grandfather was the manager of a shipyard in Fairhaven, MA and my Dad liked boats, but neither one knew a thing about sailing. I learned to sail from my Uncle Cam on a flat iron skiff that I had found on a pond where my family would spend time in the summer. The skiff would only sail downwind, so I would take off down the pond, my Dad would find me along the shore, bring me and the skiff back to the starting point, and I would take off again and again. I loved the independence and freedom.
Who have been your biggest influences as you pursued your dream?
Captain Joe Davis, of the Schooner Bill of Rights, was my mentor. I earned a position as deckhand right out of high school. Captain Davis not only taught me how to sail but about every aspect of the charter business – from how to maintain a vessel to keeping a cool head under every circumstance and how to show clients a good time. It was during that time with Captain Davis that I realized I could actually earn a living chartering my own boat. I would not have been able to build the Endeavor without the unwavering support and encouragement of my Dad. As I would sit on the deck of the Endeavor, in my back yard, wondering if I had made the right decision to build my boat, he would say, "Right or wrong – do something. Just keep going. Don't stop." And for the next two years, I didn't.
How do you even start to build a boat? Did you buy a kit?
After working on the Bill of Rights, I signed on as a deckhand aboard the research vessel Knorr from the Woodshole Oceanographic Institute. That is how I earned enough money to get my project started. From there, it was on to a job at Cape Cod Shipbuilding, to learn the craft of building boats.
After much research, I decided the Friendship Sloop would make the perfect charter boat: large cockpit for guests to relax, wide at the beam, and heavy to make her very stable. Rails low to the water allow guests to really get the full experience of being under sail.
I bought the hull, deck, and engine from Jarvis Newman in Southwest Harbor, Maine for $16,850. I had it delivered to my parent's backyard in Fairhaven, Massachusetts. We took down the white picket fence and it barely fit on the lawn. This was not a kit. I hand chose, milled, and installed each piece of wood. I completed the wiring, plumbing, rigging, and engine work. The mast and spars were custom-built by Ralph Stanley in Maine. It was indeed an Endeavor to build.
Why did you choose Nantucket to start your business?
Well, Nantucket kind of chose me. After earning my Captain's license, it was time to make some money. I began my business by offering weekly charters out of Mattapoisett, Massachusetts. After two seasons I soon found that there was not enough demand for weekly charters in that area. I was getting discouraged and was ready to sell the Endeavor and give up on my dream. In 1981, I fortuitously took my family sailing around the Cape and Islands. It was on this trip that we docked in Nantucket for a few days. When my family was exploring downtown and I was doing chores on the boat, a gentleman came by and asked if I would take him sailing for an hour or so. He offered me more than the cost of one of my weekly charters. My brother Charlie, who was very business-minded, was with me and said, "Jim this is where you need to be." With the help of the Dockmaster, I rented a slip on Straight Wharf in 1982 and after some 20,000 or more trips later, I'm still here! I am very grateful for the year-round residents and visitors that have supported me and my family these past 38 years.
What is your favorite part of the business?
After all this time, I still love to sail. The movement, the changing weather, the challenge of making first-time sailors comfortable, and getting seasoned sailors to appreciate the unique characteristics of the Friendship Sloop. People ask if I get bored or desire to go on a great sailing adventure, and I don't. Before coming to Nantucket I sailed Endeavor to Key West and up to Maine several times. As a deckhand on the Knorr, I sailed as far as the Portuguese Azores. I also love meeting people from all over the world, helping them slow down, relax and giving them suggestions on enjoying the simple things that the Island has to offer.
What is the most difficult part of the business?
That would be the boat traffic. Who likes any kind of traffic, right? Saying goodbye to my crew at the end of a season is always a tough one. We spend many, many hours together and they become part of the Endeavor family. The former crew now bring their children for a sail and last year the daughter of one of my former crew became part of the team.
Who are some of the most interesting people you have met or some of your most interesting trips?
These special stories are best shared aboard Endeavor! Get in touch to reserve a trip.
Where will we find you in the off-season?
Right here on the island. I have a barn on my property where the Endeavor is stored for the winter and I can do the maintenance. I have former crew come for a working vacation in the winter to help. I take long walks with my Golden Retriever, Tucker, fly model airplanes, and build model sailboats and half hull replicas of whaleships. My favorite off-island travels take me to the southwest for hiking, visits with my daughter Lisa who lives in Brookline, Massachusetts, and my son James who attends Coastal Carolina University in Conway, South Carolina.
Have another question?
We’d love to hear from you!
Cover photo © Roaming Fin Media