Arey’s Pond Sailing School

We have been teaching sailors on Little Pleasant Bay since 1964.

We teach private sailing lessons for students of all ages and abilities on our 14’ Arey’s Catboats. Students also have the opportunity to take lessons on our 16′ Arey’s Cabin Lynx catboat. Catboats are the traditional sailboats of Cape Cod. They are gaff rigged, very stable, and with only one sail, make perfect vessels for sailors of all ages and skill levels. Our catboats can take up to three students at once.  All of our instructors have years of experience teaching sailing. 

For those with adequate previous sailing experience we offer two hour and half day (four hour) rentals on our 14′ and 16′ catboats. Both models offer space for up to four adults and are sailed in beautiful Little Pleasant Bay.

To book a sailing lesson or rental, please see our online booking portal below. If you have any questions you may call our office at 508-255-0994 or email the sailing school at

Lesson Pricing

  • Single Private Lessons: $175/2 hr lesson, additional students $25/each
  • We offer a multi-lesson discount of five lessons for the price of four, when all five lessons are purchased at once. 5 for 4 lessons cannot be purchased online at this time, please call us to purchase.
    • The Fine Print: The 5 lessons for the price of 4 discount is only applicable for the season in which the lessons are purchased. We recommending scheduling all five lessons when purchasing the package as our schedule fills up fast and unused lessons expire at the end of the season (September of the purchase year).

Rentals Pricing

  • 2 Hour Rental
    • 14′ Catboat – $150
    • 16′ Catboat – $180*
  • Half Day Rental (4 hr)
    • 14′ Catboat – $240
    • 16′ Catboat – $270*

*Only one 16′ catboat is available to rent. Please call to confirm availability.

Book Sailing Lessons and Rentals Below

If you would prefer to book over the phone please call our office at 508-255-7900.