Sailing School & Rentals

Arey’s Pond Sailing School has been teaching sailing on Pleasant Bay since 1964. We teach all aspects of sailing, from the fundamentals to the advanced skills needed for racing, on our 14’ and 16’ Arey’s Pond Catboats. Catboats are the traditional sailboats of Cape Cod. They’re safe and stable, making them perfect for sailors of all ages. All of our experienced instructors are certified by US Sailing.

Come explore Pleasant Bay with us today! Call (508) 255-7900 for more information,  to register for a lesson or schedule a rental.

Download Pricing Sheet

Summer 2015 Photo

Summer 2015 Photo

Boat Rental Information and Rates

Explore Pleasant Bay and the Namequoit River on our rental boats. See the table below for rental options and pricing.

14′ Catboat Rental Cost: $60 – 1 hr / $190 – 1/2 day
Daysailer Rental Cost: $60 – 1 hr / $190 – 1/2 day
Single Kayak Rental Cost: $25 – 1 hr / $55 – 1/2 day
Paddle Board Rental Cost: $25 – 1 hr / $55 – 1/2 day
Gloucester Gull Row Boat Rental Cost: $10 – 1 hr / $40 – 1/2 day
Tandem Kayak Rental Cost: $35 – 1 hr / $75 – 1/2 day


Sailing School Information and Rates

Arey’s Pond Sailing School offers group lessons for students ages 8-18. These classes are held in weekly sessions, Monday through Friday from 9:30-11:30am. They offer a combination of classroom learning and hands-on learning. Our program emphasizes fun and safety and we work with students of all skill levels and sailing backgrounds.

Additionally, we offer private lessons for students of all ages. These one on one lessons are done entirely on the water with our US sailing certified instructors. Our Instructors work with students of all skill levels to identify personal sailing goals, and achieve them! Private lessons are offered by appointment, daily from 9am until 5pm and typically last for 2 hours.

Group Lessons (ages 8-18) Five, 2-hour lessons, Monday through Friday 9:30 – 11:30 AM Cost: $240.00 per person
Private Sailing Lessons Every day by appointment; 9:00AM – 6:00PM
2 hours recommended
$72 per hour
$12 per hour for each additional person



Life jackets are worn by all students from the point of departure to the point of return. Arey’s Pond Sailing School provides life jackets, however, bringing your own is suggested for the best fit and comfort. All of our sailing instructors are certified by US sailing and are trained in first aid and CPR.

Sailing School & Boat Rental Photos

Sailing School & Boat Rental Videos

Arey’s Pond Boat Yard from emilie inc. on Vimeo.