Sailing School & Rentals

In 2017, we will be celebrating our 53rd year of teaching sailing to all ages. Sign up and join us for some fun at the tiller of an Arey’s Pond Catboat or Sloop on Little Pleasant Bay. To get started read our sailing school letter and book a sailing lesson. For more information call 508-255-0994 or 508-255-7900 or email

Our goal at Arey’s Pond Sailing School is to instill confidence in your sailing ability with certified instructors in an environment that is safe, relaxed, fun and challenging. Even if you have no prior sailing experience, Arey’s Pond Sailing School can teach you to become an Old Salt in just a few lessons! Scroll down to see prices and book your lesson now.

Download our Brochure

Summer 2015 Photo

Summer 2015 Photo

Boat Rental Information and Rates

We now have a waterfront area for recreational activities. We offer kayak and paddle board lessons, and we hope to offer tours of the Pleasant Bay area in the near future. These activities are great fun when there is no wind to sail. This new area also offers a nice place to relax after a day on the water. We have a picnic table and grill available for customers use.

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 young sailors between the ages of 7 and 18 years old. Classes are held Monday through Friday each week in July and August and offer a combination of classroom instruction and hands-on learning with certified instructors. In case of poor weather, students in group classes work in our Land School, exploring topics such as knot tying, nautical terminology, rules of the road, sailing tactics, rigging and boating safety. Arey’s Pond Sailing School students learn how to become safe and skilled sailors in a fun environment. Besides learning how to sail, young sailors have the opportunity to learn important life skills such as self-confidence, self-reliance and teamwork.

Arey’s Pond Sailing School offers lessons for students of all ages with private lessons for individuals, couples, or groups.  Private lessons are offered by appointment and can take place in your boat or ours. Our ever-expanding fleet includes 12′, 14′ and 18′ sailboats including our own Arey’s Pond Cats. Private classes are designed to meet your needs and level of experience and will give you the opportunity to learn how to sail quickly and with confidence. Learn to sail with Arey’s Pond Sailing School and you’ll develop a lifetime love for the sport of sailing!

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 will be 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 life jacket is suggested for the best fit and comfort. Friday is race day; if the launch is available, we can transport parents out for viewing.

Gift Certificates Available Upon Request. For more information please call 508-255-7900 or email

Sailing School & Boat Rental Photos

Sailing School & Boat Rental Videos

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