Adult Sailing at The WaterFront Center

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.

Find Your Starting Point View Season Passes

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.

Choose Your Starting Point

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

Try sailing → Learn to sail → Complete your Check Out Sail → Rent or join social sailing

Brand new to sailing?

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

Start Here

Ready 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.

View Group Instruction

Already know how to sail?

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

Book Check Out Sail

Want one on one instruction?

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

Private Lessons

Want to sail often?

Explore Community Open Sail, Women on The Water, and season pass options for approved sailors.

View Passes

Looking for Advanced Keelboat?

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

Basic Keelboat

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 View Before Booking

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.

Please note: Passing a Check Out Sail is not guaranteed after one 6 hour session. Sailors may need additional practice or may need to take the course more than once before they are proficient enough to rent independently.

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
  • 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.
$250 per person for 6 hours of instruction
View Group Instruction

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
$250 per lesson
Request Private Lesson Dates View Before Booking

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
$50 per sailor
Book a Check Out Sail View Before Booking

Returning Sailor Exam

Returning sailors who completed a Check Out Sail in 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
$10 per sailor
Take the Returning Sailor Exam

Season Passes

Planning to be on the water often this season? The WaterFront Center offers pass options for sailors, social sailing participants, and community members who want more access to sailing and paddling throughout the season.

Community Sailing Season Pass

For approved sailors who have completed their Check Out Sail and want regular access to Community Open Sail throughout the season.

  • For approved sailors only
  • Designed for sailors who want to sail socially and regularly
  • No instructor during this program
$850

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

View Community Sailing Pass

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 group sailing offered weekly
  • For approved women sailors who have completed their Check Out Sail
  • Welcoming social sailing environment
  • No instructor during this program
$550

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

View Women on The Water Pass
Booking with your season pass: When booking your Women on The Water sessions, look for the area that says, “If you have a code for a Full Season Community Sailing Pass, enter it here:” before checking out. Enter your season pass code there so your session balance is reduced to $0 before completing checkout.
Book Women on The Water Dates
New This Season

All Access Season Pass

Make the most of the season with one pass that includes access to adult sailing opportunities and paddling.

Sign up now and receive a free sailing burgee.
  • Includes Intro to Sailing
  • Includes Group Instruction
  • Includes Community Open Sail
  • Includes Women on The Water for eligible participants
  • Includes rentals of paddleboards and kayaks
$1,500

Purchase is available without a Check Out Sail.

Sign Up for the All Access Pass

Community 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’s 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.

Price $150 + tax / 3 hours
Additional Hours $50 per hour
Capacity 2 person minimum / 4 person maximum
Boat Length 23 feet
  • 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 Rentals
Advanced Course

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 and have been certified to rent our Sonars.

  • 16 total instructional hours
  • Four 4-hour sessions
  • Additional time for practical and written testing
  • Minimum of 2 participants required
$740
Learn More About Basic Keelboat

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 Season Passes

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