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Private Sailing Lessons

Over the years we have had several smaller sized sailboats used strictly for sailing lessons. If you are starting out learning to sail, the most economical approach is on a smaller sized sailboat. Stay tuned, we might add a smaller lesson boat again in the future.

We offer lessons (2 & 4 hour) on a 42′ blue water high-end boat (Hallberg-Rassy) ideal for those that are looking to learn how to handle a larger sized boat and for those considering purchasing a larger sailboat.

You can take as many as 6 people on these lessons, those wishing to participate and/or those wishing to enjoy time on the water. Select between 2 and 4 hour options. Lots of options some including: basic to advanced sailing skills, ocean cruising, river adventures, docking, navigation and planning longer trips.

Lesson Boat

a small boat in a large body of water

The sailing vessel Mistress is a 42-foot Hallberg-Rassy, renowned for its sturdy construction, superb craftsmanship, and signature seaworthiness. Mistress provides sailing charters from the Kennebunkport location. Designed to carry ten passengers, Mistress is easy to handle and globally respected for its elegant lines and spirited performance. Comfortable for young children and seniors alike, Mistress sleeps seven and offers all the comforts of home. Equipped with a heater for warmth when needed, the boat provides a cozy environment both below and above deck. Explore photos of Mistress in the gallery below and throughout our website.

Meet Your Sailing Instructor

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.

Bob is passionate about helping people to develop their confidence and skills on the water.  His teaching experience as a Dale Carnegie instructor and providing sailing training for over 20 years allows him to figure out how provide each person a customized experiences that is centered on each persons individual learning styles.

Person in red jacket sailing during sunset on calm water.

Sailing Lesson Options