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

  • Private Lessons: $175/2 hrs, additional students $25/each

Rental Pricing

  • 14′ Catboat: $150/2 hrs; $240/4 hrs
  • 16′ Catboat: $180/2 hrs; $270/4 hrs

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.

New time slots have been added! Please call 508 255 0994 or email if you have any questions.

We look forward to welcoming you this summer!