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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

Montauk Boat Ride

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.


$395 base price(includes first student)

$105 for each additional student

Maximum 4 students

3 hours

10am - 1pm2 - 5pm

Reservations required

Private Sailing Lessons

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. 

$395 base price (includes first student)

$105 for each additional student

Maximum 4 students

3 hours

10am - 1pm2 - 5pm

Reservations required

Learn to sail in Montauk on your own private sailboat
Intro to Sailing
Basc Sailing Packages
Take one of our ASA courses on a sailboat in Montauk.

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.

Fleet Skipper Workshop

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

$395* base price (includes first student)

$105 for each additional student

*book a package of 5 lessons and receive $100 discount.

Maximum 4 students

3 hours

10am - 1pm2 - 5pm

Reservations required

Grab your friends and learn to sail in Montauk.
Women's Sailing

This sailing program offers a supportive environment for women of all skill levels to learn the art of sailing and build confidence on the water. 

During these weekly workshops you'll learn the fundamentals of sailing, safety procedures, and more while connecting with like-minded women and enjoying time on the water. Each session consists of 4 workshops, held on Wednesday evenings.


The lessons are taught aboard Catalina 22 sailboats equipped with a tiller and outboard engine. These boats are ideal for learning and perfecting sailing skills, as they are sturdy keelboats that do not capsize. Along with all required safety equipment, they also have creature comforts such as cockpit cushions, bluetooth speaker, marine restroom, and an enclosed cabin with seating area and cooler.

Subjects to be covered:

  • -parts of the boat

  • -fundamentals of sailing

  • -tacking/gybing

  • -basic sailing terminology

  • -knot tying and line handling

  • -basic rules of the road

  • -key navigational aids


1st Session 

June Workshop dates:

6/5, 6/12, 6/19 & 6/26


2nd Session

July Workshop dates:

7/3, 7/10, 7/17, 7/24

Wednesday Evenings, 6-8pm

Reservations required

$360* pp 

*due to limited open spots this workshop is non refundable but is transferable. 

Join us for a women's sailing program in Montauk.
ASA logo
Montauk Boat Rides, Lessons, and Tours.

Come Sail Montauk with us!

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