So Many Ways to Learn
Beginner and Intermediate Sailing Classes with Certification . . .Out on the Water Sailing has implemented a comprehensive, intuitive and fun curriculum to help you learn the ropes. With a small amount of classroom training, our goal is to get you on the boats quickly to learn and apply basic sailing principals. Both experienced sailors with American Sailing Association instructor certifications, Chris and Toby can work with varying skill levels to help you become confident. Our boats, among the best performing sailboats ever built, are rigged and maintained with safe and easy teaching in mind. We can also help students attain internationally recognized sailing certifications through our affiliate schools.
Introduction to Sailing
Do you think you might be interested in sailing? Never been on a boat before? Our Introduction to Sailing Course is designed to be an affordable way for you to decide if sailing is something that you would like to explore further. The session is 2-3 hours long on Wanderlust. We will go over the very basics of safety, terminology, and of course, get a great view of Manhattan.
$295 for a group of 3 people
Basic Sailing
By the end of this 3-day course based out of New York harbor, you’ll have the tools and basic experience necessary to start enjoying sailing out on the water.You will have learned the basics of a 22ft keelboat and will be able to use it on your own. No prior navigation or sailing experience is necessary for this course. To sign up for Basic Sailing, view our schedule.
$495 per person
Basic Coastal Cruising
The Basic coastal cruising course is also a 3-day course held in New York Harbor that builds on the experience you gained in Basic Sailing and uses the J22 keelboat. Areas of instruction include: Safety, Rules of the Road, Weather, Seamanship, Gear & Equipment and Duties of the Skipper & Crew. There will be many more sailing exercises and fun aboard the small keelboat. To sign up for Basic Coastal Cruising, view our schedule.
$495 per person (local)
$795 per person (destination)
Charter Course
Out on the Water Sailing's Charter Course brings your previous experiences in Basic Sailing and Basic Coastal Cruising together to provide the skills needed for extended cruising and chartering a boat for your own. This 3-day course, aboard the 42' sloop, Pearl, will give you the tools and experience needed to set out on your own voyage. Students will also stay aboard, cruise to some great ports, and share in all the duties one has when cruising. Objectives of this course include: planning the cruise, living afloat, weather, knots, seamanship, Navigation and Knowledge of Boat Systems, and Maintenance. Basic Coastal Cruising and Basic Sailing are required to take this course. The course is offered out of eastern Long Island Sound and during some destination charters. To sign up for our Charter Course, view our schedule.
$795 per person (destination)
Performance Sailing
There is a reason we use boats that are known for great performance. We LOVE to sail. We offer performance sailing workshops to bring students beyond the basics of sailing and cruising and teach the essence of sailing and how to sail faster. This course focuses on downwind sailing using spinnakers, advanced sail trim for both upwind and downwind sailing, proper tuning of a boat for speed, reefing, heavy wind technique and proper weight distribution. The course also provides an introduction to sailboat racing. Our philosophy in this course is that a sailboat is akin to a fine instrument that needs proper tuning to properly harness the wind. Wanderlust and Pearl both make the perfect platforms for this course. To sign up for Performance Sailing, view our schedule.
$75 per hour
Individual Lessons
Out on the Water Sailing can provide individual lessons to beginning sailors and experienced sailors alike on our boats or yours. Our individual lessons focus on you, your strengths and weaknesses, and your goals. We can give you the tools and expertise to confidently take your sailing to the next level. Whatever your objectives are, Out on the Water has the experience to help you along the way. please contact us.
$75 per hour











