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Old Quarry Sailing School



•Basic Sailing  •Intermediate Sailing   •Private Lessons  •Our Instructors

All classes require advanced registration. Please contact us for a schedule and to sign up. The boats we use for classes are the Cape Dory 19. Gratuities for instructors are greatly appreciated.

Basic Sailing



Children and Young Adult Classes


10 hours (2.5 hours each day for 4 days), $200 per student. 3 person minimum.

With student/teacher ratios of no more than 4:1 students will learn to steer in a variety of boats that fit their size and skill. Then with an emphasis on Safety, Fun and Learning, you will learn the true life sport of sailing. Our goal is to have each student sailing their own boat within a week.

Adult Classes


6 hours ( 3 hours each day for 2 days), $120 per student. 3 person minimum.

Learn to operate a small sailboat in the protected waters of Webb Cove in a variety of weather conditions. On and off the water lessons will teach you how to safely and efficiently leave a mooring, or dock, maneuver through the points of sail, and return from various angles. You will be introduced to sailing terms, theory, techniques, and hands-on application. Nor more than 4-5 students plus instructor per boat.

Intermediate Sailing



Children and Young Adult Classes


5 hours (can do in 1 day or split into 2 days), $100 per student. 3 person minimum.

If you've already taken our Basic Sailing class or have had other formal training in sailing, but need additional instruction and practice on the water, you can enroll in Intermediate Sailing. This will combine a review of sailing principles and techniques to gain the confidence you need to be a better sailor. Refine your skills in trimming the sails, reading the wind and water, and developing a better understanding of sailing theory. No more than 4-5 students plus instructor per boat. Private lessons are also offered.

Adult Refresher


5 hour s(can do in 1 day or split into 2 days), $100 per student. 3 person minimum.

If you've taken sailing lessons before or learned how to sail on your own but want time on the water with an instructor to brush up on your skills, this Adult Refresher course will help you do that. Offered each week, you can sign up for one session or several. You will review safety procedures and right-of-way rules, gain more confidence in your sailing ability and more. No more than 4-5 students plus instructor per boat. Private lessons are also offered.

Adult Quicky Tune Up Refresher


$36 per hour per student. 3 person minimum.

One hour minimum, two hours is preferable. This is for experienced sailors who are rusty and just need a bit of a refresher to be safe on the water. The instructor will go over the rigging, take you out for a spin, go over the basics, and show you around the area so that you can be safe and feel comfortable.

Private Lessons


1 person: $60/hour/person
2 people: $42.50/hour/person
3 people: $36/hour/person
4 people: $33/hour/person

We offer personalized training to fit your skill level, sailing interests, and specific needs. Private lessons are available for children, adults, families, teams and special groups from basic to advanced sailing. Reservations required. Lessons are booked in a minimum of 2-hour time slots.

Our Instructors



Jessica Naylor


An avid sailor for nearly 20 years, Jessica is a member of the US Sailing Association. She attended the US Sailing Program for instructors of sailing lessons in small sailboats. Jessica has been teaching sailing lessons for the past 8 years here at Old Quarry.

All classes require advanced registration. Please contact us for a schedule and to sign up.


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