Adult Sailing at The WaterFront Center

Sail Oyster Bay This Season

From your first sail to independent time on the water, The WaterFront Center offers a clear pathway for adults to learn, practice, rent, and keep sailing.

Find Your Starting Point Rent a Sailboat

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. Lesson and rental requests open Memorial Day Weekend, with sailing opportunities available throughout the season.

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Good to Know Before Booking

You may see a message that says, “This experience is fully booked. Add your guest and contact information to join the waitlist.”

Please still complete the waitlist form. This is how we are collecting lesson and program requests for the season.

Sailors may join the waitlist for as many dates and times as they are interested in. When a program date and instructor become available, our team will contact sailors in the order requests are received.

Once contacted, sailors will have 24 hours to reply, confirm, and pay before the spot is forfeited and offered to the next person.

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Choose Your Starting Point

Not sure where to begin? Use this quick guide to find the best fit.

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Brand new to sailing?

Start with Intro to Sailing for a relaxed first experience on Oyster Bay.

Start Here

Tried sailing and want to learn?

Move into Group Instruction, our 6 hour Learn to Sail course.

View Group Instruction

Already know how to sail?

Book a Check Out Sail to begin the rental approval process.

Rent a Sailboat

Want one on one instruction?

Book a Private Lesson to work on your personal sailing goals.

Private Lessons

Completed your Check Out Sail?

Explore rentals, passes, Community Open Sail, and Women on The Water.

Social Sailing

Want formal certification?

Basic Keelboat is the next step for experienced sailors seeking certification.

Basic Keelboat
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Available Times

The following times apply to Intro to Sailing, Private Lessons, and Check Out Sails. Full availability for these sailing experiences begins Memorial Day Weekend.

10:00 AM 12:00 PM 12:30 PM 2:30 PM 3:00 PM 5:00 PM 5:30 PM

Your Adult Sailing Pathway

Try sailing, learn the skills, complete your Check Out Sail, then keep sailing through rentals, passes, and social sailing opportunities.

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1

Intro to Sailing

A first sailing experience for new or beginner sailors.

2

Group Instruction

A 6 hour Learn to Sail course to build skills toward sailing independently.

3

Check Out Sail

Complete rental approval after instruction or as an experienced sailor.

4

Rentals and Passes

Approved sailors can rent or use monthly and season passes.

5

Social Sailing

For experienced sailors who have completed their Check Out Sail.

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Intro to Sailing

This two hour sail with an instructor is designed to introduce new sailors and beginner sailors to sailing. It is a great first experience on Oyster Bay.

Please note: Intro to Sailing is not an instructional sail. Customers are limited to one Intro to Sailing booking.

  • Two hour sail
  • Instructor aboard
  • Up to 4 people per boat
  • One Intro to Sailing booking per customer
$150 for up to 4 people
Request Intro to Sailing
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Learn to Sail and Prepare to Rent

Group Instruction

After trying Intro to Sailing, sailors who want to continue learning can move into Group Instruction.

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 6 hour Learn to Sail course helps sailors build confidence on the water and prepare for their Check Out Sail.

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Course Schedule

  • 6 hours of instruction
  • Weekday option: Tuesday, Wednesday, and Thursday from 6:00 PM to 8:00 PM
  • Weekend AM option: Saturday and Sunday from 10:00 AM to 1:00 PM
  • Weekend PM option: Saturday and Sunday from 1:00 PM to 4:00 PM
  • This course is completed as one full scheduled series. Please choose the weekday or weekend option that works best for your schedule, as make up classes are not available.
  • Includes a Check Out Sail after the course
$250 per person for 6 hours of instruction
View Group Instruction

Best For

This course is a strong next step for adults who enjoyed Intro to Sailing, beginners ready for a full Learn to Sail course, or returning sailors who want a structured refresher before working toward rental approval.

Group Instruction Covers

This course is designed to help sailors build practical skills, confidence, and readiness to sail more independently.

Foundational Skills

  • Sailing terminology
  • Rigging and de-rigging
  • Sail trim
  • Tacking and gybing
  • Reading telltales

Safety and Boat Control

  • Sea safety
  • Marine navigation basics
  • Heave to
  • Reefing
  • Man overboard procedures

Rental Readiness

  • Solo rigging practice
  • Mooring skills
  • Leaving and returning to the mooring
  • Confidence building on the water
  • Check Out Sail included after the course
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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
$250 per lesson
Request Private Lesson Dates

Build confidence on the water.

Whether you are learning, refreshing your skills, or preparing to rent, our adult sailing pathway helps you take the next step.

Check Out Sails and Sailboat Rentals

Approved sailors can enjoy time on Oyster Bay Harbor through sailboat rentals, monthly rental passes, and season rental passes.

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Check Out Sails and Sailboat Rentals

Ready to rent a sailboat? 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.

  • Required for new renters
  • Required if you have not completed a Check Out Sail with us in 2024 or 2025
  • 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
Book a Check Out Sail

Returning Sailor Exam

Returning sailors who completed a Check Out Sail in 2024 or 2025 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
Take the Returning Sailor Exam

Sailing Rental Monthly and Season Passes

Planning to sail often this season? Monthly and season passes are available for eligible sailors who have completed the rental approval process.

  • For approved sailors only
  • Available for sailors who complete a 2026 Check Out Sail
  • Available for eligible returning sailors from 2024 or 2025
  • Rental approval must be complete before using a pass
View Rental Passes
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Social Sailing

Community Open Sail and Women on The Water are social sailing opportunities for experienced sailors who have completed their Check Out Sail. Registration is available on separate program pages once a sailor has completed their Check Out Sail.

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Community Open Sail

Community Open Sail is designed for sailors who already have sailing experience and are ready to enjoy time on the water with other approved sailors.

This social sailing program is for participants who have completed their Check Out Sail and are comfortable sailing with others aboard The WaterFront Center’s Sonars.

  • For approved sailors who have completed their Check Out Sail
  • Participants sail together as a crew
  • Crews are responsible for rigging, de-rigging, sailing, and mooring
  • No instructor during this program
  • A launch operator will be on the dock to bring sailors to and from the Sonars

Sailors will have access to register once their Check Out Sail is complete.

$65 for 2 hours or $85 for 3 hours
View Community Open Sail

Women on The Water

Women on The Water is designed for women who already have sailing experience and are ready to continue sailing in a welcoming, social setting.

This program follows the same social sailing format as Community Open Sail and is for approved women sailors who have completed their Check Out Sail.

  • For approved women sailors who have completed their Check Out Sail
  • Participants sail together as a crew
  • Crews are responsible for rigging, de-rigging, sailing, and mooring
  • No instructor during this program
  • A launch operator will be on the dock to bring sailors to and from the Sonars

Sailors will have access to register once their Check Out Sail is complete.

$65 for 2 hours
View Women on The Water
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Advanced Course

US Sailing Basic Keelboat Certification

Basic Keelboat is an advanced course for experienced sailors who want to achieve the US Sailing Basic Keelboat Certification.

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Basic Keelboat

This program is the next step for individuals who have already completed Group Instruction and have been certified to rent our Sonars.

  • Best for experienced sailors
  • Designed for sailors seeking formal certification
  • Next step after Group Instruction and rental certification
  • Price to be announced
Learn More About Basic Keelboat
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Which option should I choose?

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1

I am new to sailing.

Start with Intro to Sailing for a relaxed two hour introduction to sailing on Oyster Bay.

2

I tried sailing and want to learn more.

Move into Group Instruction for a 6 hour Learn to Sail course designed to build foundational skills and prepare you for the Check Out Sail.

3

I want personalized instruction.

Choose a Private Lesson to work directly with an instructor on your personal sailing goals.

4

I want to rent a sailboat.

Complete a Check Out Sail, or take the Returning Sailor Exam if you completed a Check Out Sail in 2024 or 2025.

5

I want to keep sailing socially.

Once your Check Out Sail is complete, you will have access to register for Community Open Sail or Women on The Water through their separate registration pages.

6

I want formal certification.

Basic Keelboat is the next step for experienced sailors seeking US Sailing Basic Keelboat Certification.

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Ready to get on the water?

Select the program that fits your goals and request your preferred dates. Our team will contact sailors in the order requests are received when a program date and instructor become available.

Start with Intro to Sailing View Group Instruction View Sailing FAQs

Questions? Call 516 922 SAIL or email sailing@thewaterfrontcenter.org.