Learn to sail at your own pace with private instruction or check out one of our classes for adults or junior sailors


Sail Montauk is certified sailing school, accredited with the American Sailing Association. We've got something for every level, from first timers to experienced sailors looking to refresh their skills. The waters of the Hamptons are the perfect place to learn to sail.

If you would like to brush up your skills aboard your own sailboat, check out our Consultation Services.


Cruise Montauk with us!

All lessons include:

  • A Licensed Captain/Instructor

  • Cooler with Ice & Water


Learn at your own pace with a personal instructor aboard a 22 ft sailboat. Perfect for beginners or if you're just a bit out of practice.


$330 base price(includes first student)

$90 for each additional student

Maximum 4 students

3 hours

10am - 1pm2 - 5pm

Reservations required


Purpose: To test the waters if you’re unsure about committing to the full Basic Sailing Course. 

How it works: This is the first class in the Basic Sailing Course Package. This class covers knot tying, terminology and on the water practice. If you decide to continue your lessons, this session can be applied to the Basic Sailing Course Package. 

$330 base price (includes first student)

$90 for each additional student

Maximum 4 students

3 hours

10am - 1pm2 - 5pm

Reservations required

Sailing Lessons

Sign up for a minimum of 5 Private Lessons and we'll include the American Sailing Association Basic Keelboat Sailing ASA 101 course material, test, and certification fee. Our instructors are certified professionals with plenty of experience to guide you through the course.

After completing a Private ASA 101 course, you are eligible to receive 10% off Sail Montauk lessons and rentals for one year!

Subjects covered in course includes:

  • Boat Handling

    • Tacking & Jibing

    • Hoisting & Trimming Sails

    • Points of Sail

    • Docking

  • Sailing Terminology

    • Parts of the Boat

    • Sailing Jargon

  • Navigation Rules

  • Aids to Navigation

    • Sound Signals

    • Navigation Lights

    • Markers & Buoys

  • Safety Gear and Procedures

    • Recommended & Required Safety Equipment

    • Man Overboard Drills

  • Important Sailing Knots

*Must be scheduled and completed by the end of the current sailing season.


Purpose: To orient students to bareboat our rental fleet. This is for individuals who already know how to sail, and have a minimum of ASA 101 or equivalent level of knowledge and experience. 

How it works: If you’re a little nervous about renting on your own, this class will help you independently rent our rental fleet. Take as many as you need to feel comfortable.

  • Subjects that could be covered depending on your area of focus:

    • Introduce students to specific Sail Montauk boats and operations

    • Identify & demonstrate running rigging

    • Anchoring

    • Docking

    • Outboard operation & troubleshooting

$330 base price (includes first student)

$90 for each additional student

Maximum 4 students

3 hours

10am - 1pm2 - 5pm

Reservations required

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