Boats & Crew

Captain Abby discovered her love for sailing during college when she embarked on a nine-week semester at sea, navigating the Caribbean and the East Coast aboard The Spirit of Massachusetts. Abby and Bob have since taken numerous sailing courses together, with the pinnacle being an offshore training program in 2016. This program covered 1,600 miles from Svalbard to Iceland in the Norwegian Sea aboard Mahina Tiare III, a Hallberg-Rassy 45′ sloop.

Both Abby and Bob hold U.S. Coast Guard Master’s Licenses with towing and sailing auxiliary endorsements. They have owned and sailed Mistress since 2014, finding deep joy in sharing their boat and sailing experiences with all who come aboard. When their schedules align, Abby and Bob work together, offering the unique experience of two captains for the price of one.

Abby owns and operates the company and is responsible for all locations.

Captain Bob’s sailing journey began as a young boy in 1972 on Barnegat Bay, New Jersey. He fell in love with the stunning Maine coast while working aboard several Maine schooners, including the Angelique, Appledore, Mary Day, and Surprise. Bob has owned and chartered numerous sailboats, many along the picturesque Maine coast. Bob captain’s Mistress and operates primarily in the Kennebunkport location.

Captain Douglas Goldhirsch has spent his life on the water, from small boats on the Great South Bay of Long Island, NY, to large commercial vessels. His journey began at 13 when he helped build a 20-foot powerboat with his father and brother— a boat still in the family today!

As an adult, Doug became a United States Coast Guard Licensed Mariner and worked on large sail training vessels, including time with the Sea Education Association. He then spent eight years with the Hurricane Island Outward Bound School, sailing and mentoring young people along the Maine coast.

Coming ashore, Doug owned Southport Island Marine (SIM) in Boothbay Harbor, where he built a reputation as a top-tier boatbuilder and boatyard operator. Over the years, he built several Southport 30 and Southport 21 powerboats, including Avelinda, which he has run as a charter boat for over 15 years. Doug enjoys meeting new people, sharing his knowledge of the coast, and making lasting connections with his guests.  Doug leads with Nolan the Portland location.

Captain Jonathan Boyd’s sailing adventures began in the early 1980s on the Finger Lakes of New York. His professional career in opera has taken him around the world, but his passion for sailing has remained constant. In 2001, Jonathan earned his first sailing certification while navigating a 40-foot Morgan in Sarasota Bay, Florida. Jonathan works at the Kennebunkport area.

Jonathan has since raced and cruised on various sailboats in the Hudson River, NY, and along Long Island’s North and South shores. After moving to Maine, he obtained his US Coast Guard Master license with towing and sailing auxiliary endorsements. Jonathan has captained many sailboats and continues to participate in races and deliveries whenever possible. Recently, he completed the Monhegan Island race and delivered an 88-foot Ferretti motor yacht. Jonathan looks forward to meeting you, and with the right request, he might even serenade you with an aria. Check out Jonathan’s opera career website for more details.

Captain Nolan Conlin has spent his life on the water, with his passion for boating beginning at the age of 10 in his hometown of Boothbay Harbor, Maine. His dream of becoming a captain started with his first boat purchase—a well-loved 1974 Sunfish that barely stayed afloat. By the age of 12, he had joined the Boothbay Harbor High School Sailing Team, where he refined his skills and developed a deep respect for the sea.

Nolan’s extensive experience navigating Maine’s waters, combined with his enthusiasm for sharing the beauty of Casco Bay, makes him an exceptional guide for your maritime adventure. His knowledge of the area’s history, landmarks, and wildlife ensures a tour that is as informative as it is breathtaking.  Nolan co-leads with Doug the Portland location.

Captain Robin Thayer, a native Mainer, has been guiding professionally since 1995. She is a Master Maine Guide, a licensed NH fishing guide, and a USCG 25 Ton Master Captain. Captain Robin is one of the few female charter captains operating on the coastal waters of Southern Maine from the Kennebunkport location. Known for her pleasant, patient, and accommodating nature, she ensures every guest has a memorable Maine experience on the water.

Captain Shawn Tibbetts, leading our power boating Experiences in the Kennebunkport location, has been an avid outdoorsman since birth. Growing up in the Great North Woods of New Hampshire and Western Maine fueled his love for the outdoors. After proudly serving in the Marine Corps, Shawn returned to civilian life and started his charter fishing business in Saco, ME.

During the offseason, Captain Shawn enjoys hunting and driving commercial trucks. He holds a U.S.C.G. 100 Ton Masters License and is a registered Maine Guide.

Lucy began crewing with us in 2023, fulfilling a lifelong dream. Her delightful humor, infectious laughter, and love of people will make you feel right at home. As a long-time resident of Saco, Lucy knows all the best places to visit, work, eat, and enjoy, making her an invaluable addition to our team.