Sailing Programs
Explore Oyster Bay Harbor through guided sails, private instruction, certification courses, and community sailing opportunities.
The WaterFront Center offers sailing instruction for all experience levels — from complete beginners stepping aboard for the first time to seasoned racers refining advanced skills.
As a U.S. Sailing Accredited School and Community Sailing Center, we are committed to expanding access to the sport and fostering a welcoming, inclusive environment on and off the water.
Our core sailing season runs from Memorial Day through Columbus Day. We look forward to welcoming you back in Spring 2026.
Instructor-Led Sailing Experiences
Discover Sailing: First Experiences
Explore all that Oyster Bay Harbor has to offer with a Discover Sail.
This two-hour sailing experience takes up to four guests out on the water with a certified sailing instructor. It’s perfect for first-time sailors who want to see if sailing is right for them — or for families and friends looking to enjoy a relaxing cruise together.
Program Details
2-hour sail
Maximum of 4 passengers per boat
Certified sailing instructor included
Cost: $225
Includes boat reservation and up to four passengers.
Children ages 5–17 must be accompanied by a parent or guardian.
Children under 5 are not recommended.
Scheduling & Availability
Adult sailing experiences are scheduled based on instructor availability, which is often confirmed on short notice.
Due to high demand and limited instructor capacity, we operate on a rolling interest list rather than a fixed booking calendar.
The Adult Sailing Interest List opens May 15.
Please return on or after May 15 to add your name and be included in this season’s scheduling queue.
➡️ Join the Adult Sailing Interest List (Opens May 15)
Private Lessons
Learn to sail or refine your skills with a personalized two-hour lesson tailored to your goals — from sail trim and boat handling to building confidence at the helm.
Private Lessons are available: (Instructor availability dependent)
Optimists & C420s (youth sailors under 18)
Sonars (adult sailors)
Pricing
$275 – Two-hour session (includes one sailor)
$60 – Each additional participant
Maximum of 4 sailors per session
Scheduling & Availability
Adult sailing experiences are scheduled based on instructor availability, which is often confirmed on short notice.
Due to high demand and limited instructor capacity, we operate on a rolling interest list rather than a fixed booking calendar.
The Adult Sailing Interest List opens May 15.
Please return on or after May 15 to add your name and be included in this season’s scheduling queue.
➡️ Join the Adult Sailing Interest List (Opens May 15)
U.S. Basic KeelBoat Certification
June Cohorts — Dates Released in May
Earn your U.S. Basic Keelboat Certification through this structured 16-hour course designed to build confidence, seamanship, and independence on the water. This US Sailing certification course teaches the skills required to earn your U.S. Basic Keelboat Certification.
If you complete the course and pass both the practical and written exams, your certification will document:
The skills successfully completed
The type of boat you trained on
The sailing area
Upon successful completion, you will receive:
A US Sailing certification card
An official logbook
Your logbook allows you to record each sailing experience — including conditions, location, and vessel — which may be used when renting sailboats outside of The WaterFront Center.
Course Structure
16 total instructional hours
Four 4-hour sessions
Additional time for practical and written testing
Minimum of 2 participants required
Those with little sailing experience will complete the full program.
Includes
Boat reservation (one sailor for the full course)
US Sailing Basic Keelboat textbook
Logbook
Certification testing
One credit toward a WFC Community Sailing class
One-year US Sailing membership (contingent upon passing)
Cost: $740
Registration
Enrollment opens once the June course dates are published in May.
Are you a Parent? Looking for Programs for your Children?
Visit our Youth & Family Programs page to find activities, programs, and resources more suited for individual families.
Community Sailing
Season Pass
Can’t get enough of Community Sailing? Save money with a Season Pass!
Community Open Sail
Sail, Learn & Connect!
Brush up on your sailing skills, meet fellow sailors, or simply enjoy a beautiful day on the water in Oyster Bay Harbor! Whether you're a beginner or an experienced sailor, our on-water instructor will be there to answer questions and help you refine your technique.
Schedule
Wednesdays: 6:00 PM – 8:00 PM
Saturdays: 1:00 PM – 4:00 PM
Sundays: 10:30 AM – 1:30 PM
2-hour and 3-hour sail options available.
Details
For adults 18+
Reservations required (no walk-ins)
Women on the Water (WOW)
Sail, Connect & Unwind!
Women in our community are invited to enjoy an evening of sailing in a fun, safe, and supportive environment! Whether you want to learn the basics of sailing, meet new friends, or simply relax on the water, this is the perfect opportunity to cruise Oyster Bay stress-free aboard our Sonars.
Schedule
Thursdays: 6:00 PM – 8:00 PM
Details
For women 18+
Reservations required (no walk-ins)
If WOW is fully booked, Community Open Sail sessions are available as an alternative.
Open Community Sailing – Full Season Pass
Unlimited Open Sail sessions from Memorial Day weekend through the end of the season.
Women on the Water – Full Season Pass
Unlimited WOW sessions from Memorial Day weekend through the end of the season.