Sail Oyster Bay
From your first sail to weekly outings on the water, The WaterFront Center offers a clear pathway for adults to learn, practice, rent, and keep sailing all season long.
Adult Sailing Programs
The WaterFront Center offers sailing opportunities for a range of experience levels, from complete beginners stepping aboard for the first time to returning sailors preparing to rent and experienced sailors looking to sharpen their skills.
As a U.S. Sailing Accredited School and Community Sailing Center, we are committed to expanding access to the sport and creating a welcoming, inclusive environment on and off the water.
Our core sailing season runs from Memorial Day Weekend through Columbus Day. Fall Adult Sailing is open now, with lessons and Check Out Sails available for direct booking. Select your program below to view currently available dates and register.
Choose Your Starting Point
Not sure where to begin? Use this quick guide to find the best fit.
Brand new to sailing?
Start with Intro to Sailing for a relaxed first experience on Oyster Bay Harbor.
Start HereReady to learn to sail?
Start with Group Instruction, our 6 hour Learn to Sail course. Intro to Sailing is a great first experience, but it is not required before taking this class. Women-only sessions are also available on select dates.
View Group InstructionAlready know how to sail?
Book a Check Out Sail to begin the rental approval process.
Book Check Out SailWant one on one instruction?
Book a Private Lesson to work on your personal sailing goals.
Private LessonsWant to sail often?
Explore Community Open Sail, Women on The Water, and season pass options for approved sailors.
View PassesLooking for Advanced Keelboat?
U.S. Sailing Basic Keelboat is the next step for experienced sailors seeking certification. 2026 sessions have concluded.
Learn About Basic KeelboatIntro to Sailing
Enjoy a two-hour introductory sail on Oyster Bay Harbor with a certified instructor. One booking reserves the entire boat for up to four guests.
Please note: Intro to Sailing is an introductory sailing experience rather than a full instructional lesson. Customers are limited to one Intro to Sailing booking.
- Two-hour introductory sail
- Certified instructor aboard
- One booking reserves the entire boat
- Up to 4 guests
- One Intro to Sailing booking per customer
$150 reserves the entire boat for up to four guests.
Learn to Sail
Group Instruction
Group Instruction is our 6 hour Learn to Sail course for adults who are ready to build sailing skills and work toward sailing more independently. Sailors do not need to take Intro to Sailing before enrolling in this course.
Designed to build strong foundational sailing skills, this course is appropriate for beginners or sailors who want a refresher. Participants receive a thorough introduction to sailing terminology, rigging and de-rigging, basic sailing maneuvers, sea safety, and marine navigation aboard a Sonar keelboat.
This course helps sailors build confidence on the water and prepare for their Check Out Sail.
Course Schedule & Registration
- 6 hours of instruction
- Available course dates and times are shown during registration
- This course is completed as one full scheduled series; make-up classes are not available
- Includes a Check Out Sail after the course
- Passing the Check Out Sail is not guaranteed after one course. Additional practice or repeat instruction may be needed before a sailor is approved to rent independently.
Best For
This course is a strong next step for adults who are new to sailing, beginners ready for a full Learn to Sail course, sailors who enjoyed Intro to Sailing and want to continue, or returning sailors who want a structured refresher before working toward rental approval.
Group Instruction Covers
- Sailing terminology
- Rigging and de-rigging
- Sail trim, tacking, and gybing
- Reading telltales
- Sea safety and marine navigation basics
- Heave to, reefing, and man overboard procedures
- Mooring skills and leaving and returning to the mooring
Private Lessons
Private lessons are instructional sessions with an instructor on the Sonar. This is the best option for sailors who want to sharpen specific sailing skills through a customer driven agenda.
- Instructor aboard the Sonar
- Personalized instruction
- Great for skill building and refreshers
- Private lessons are not paired with other sailors
$60 for each additional attendee, up to four people total.
U.S. Sailing Basic Keelboat Certification
Basic Keelboat is an advanced course for experienced sailors who want to achieve the U.S. Sailing Basic Keelboat Certification.
This program is the next step for individuals who have already completed Group Instruction.
- 16 total instructional hours
- Four 4-hour sessions
- Two additional Community Sailing passes for practice before the written and practical certification tests
- Minimum of 2 participants required
Interested in future certification opportunities? Email sailing@thewaterfrontcenter.org.
For New & Returning Sailors
Sailors Preparing for Rentals, Community Open Sailing, and Women on The Water
Ready to begin the rental approval process? A Check Out Sail is required before renting from The WaterFront Center.
Sailors must be able to rig, leave the mooring, sail, return to the mooring, and de-rig on their own.
Check Out Sail
- Required for new renters
- Required if you have not completed a Check Out Sail with us within the last two years
- Includes a 10 question written test
- Includes an on the water practical exam
- Evaluation may include rigging, de-rigging, leaving and returning to a mooring, tacking, gybing, reefing, and safety maneuvers
- Check Out Sails may be paired with other sailors
Returning Sailor Exam
Returning sailors who completed a Check Out Sail within the last two years are eligible to take the Returning Sailor Exam instead of booking a new Check Out Sail.
- Available Monday through Friday
- 10:00 AM to 5:00 PM
- Completed at The WaterFront Center
- Results may take up to 72 hours
Plan Ahead for 2027
Interested in making sailing a regular part of your next season? Explore The WaterFront Center’s 2027 season pass options below. Registration and 2027 pricing will be announced with the new sailing season.
2027 Community Sailing Season Pass
For approved sailors who want regular access to Community Open Sail throughout the sailing season.
- For approved sailors who complete WFC’s rental approval process
- Designed for sailors who want to sail socially and regularly
- No instructor during Community Open Sail
2027 pricing and registration coming soon.
Learn About the Community Sailing Pass2027 Women on The Water Season Pass
For approved women sailors who want to take part in Women on The Water group sailing throughout the season.
- Women’s social sailing opportunities throughout the season
- For approved women sailors who complete WFC’s rental approval process
- Welcoming social sailing environment
- No instructor during this program
2027 pricing and registration coming soon.
Learn About the Women on The Water Pass2027 All Access Season Pass
Plan ahead for a full season on the water. The All Access Season Pass is WFC’s most comprehensive option for sailors who want to make sailing and paddling a regular part of their season.
- Designed to combine adult sailing opportunities and paddling access
- Includes instructional and social sailing opportunities
- Includes access to paddleboards and kayaks
- Full 2027 benefits, pricing, and registration details will be announced for the new season
2027 registration coming soon.
Learn About the All Access PassCommunity Sailing
Community Open Sail and Women on The Water are social sailing opportunities for experienced sailors who have completed their Check Out Sail. Reservations are required, and registration is available once a sailor has completed their Check Out Sail.
Sailboat Rentals
Once rental approval is complete, approved sailors can reserve one of The WaterFront Center 23-foot Sonars and enjoy independent time on Oyster Bay Harbor.
Sailboat rentals are available for sailors who have completed the Check Out Sail process or are eligible returning sailors.
- For approved sailors only
- Monthly and season pass options are available
Sailors will have access to register once their Check Out Sail is complete.
View Sailboat RentalsCancellation & Rescheduling Policy
This policy applies to Intro to Sailing, Private Lessons, Check Out Sails, and Group Instruction.
- Cancellations made at least five days before the scheduled program date are eligible for a refund, not including the processing fee.
- Cancellations made at least two days before, but fewer than five days before, the scheduled program date may be rescheduled but are not eligible for a refund.
- Cancellations made less than two days before the scheduled program date are not eligible for a refund or rescheduling.
All cancellation and rescheduling requests must be approved by the Programs Manager. Please email requests to sailing@thewaterfrontcenter.org.
Ready to get on the water?
Fall Adult Sailing is open for booking. Choose the program that fits your goals and view available dates and registration options. No waitlists.
Questions? Call 516 922 SAIL or email sailing@thewaterfrontcenter.org.