Sail Oyster Bay
Sailboat Rentals & Community Sailing
Rent a Sonar, join a welcoming group sail, or choose a pass that keeps you on the water all season.
Start Here
What do I need before I can sail?
Answer two quick questions and we’ll point you to the correct next step.
Is your sailing status currently approved by The WaterFront Center?
Choose “Yes” if you have already completed the required approval and are currently cleared to book.
Have you completed a WFC Check Out Sail within the last two years?
This determines whether you can take the shorter Returning Sailor Exam.
Do you have the current booking-page password?
The protected page contains rentals, Community Open Sail, Women on The Water, passes, and the Returning Sailor Exam.
Choose How You Sail
Clear options for every kind of sailor
Select a category to compare only the choices that matter to you.
Check Out Sail
Required if you are new to WFC rentals or have not completed a Check Out Sail within the last two years.
- Written test
- On-the-water practical evaluation
- Required before independent rentals
Returning Sailor Exam
For sailors who completed a WFC Check Out Sail within the last two years and need to renew their status.
- Monday–Friday, 10:00 AM–5:00 PM
- Completed at WFC
- Allow up to 72 hours for results
Sonar Sailboat Rental
Reserve a 23-foot Sonar and enjoy independent time sailing Oyster Bay Harbor.
- 2-person minimum; 4-person maximum
- Additional hours: $50
- Current WFC approval required
Community Open Sail
Sail with other experienced adults in a relaxed community setting.
- Adults 18+
- Reservations required
- No instructor; participants sail as a crew
Women on The Water
A welcoming weekly sailing opportunity for women with sailing experience.
- Women 18+
- Thursdays, 6:00–8:00 PM
- No instructor; reservations required
Community Open Sail Pass
Regular access to Community Open Sail throughout the season.
- Reserve each sailing date
- Participants sail as a crew
- No instructor
Women on The Water Pass
Join Women on The Water group sailing throughout the season.
- Weekly group sailing
- Reserve each sailing date
- Welcoming social environment
Sailing Rental Season Pass
Full-season rental access for sailors who want to get on the water often.
- Sail up to 4 hours every day
- Rent from the Sonar fleet
- Reservations still required
Sailing Rental Monthly Pass
One month of frequent Sonar rentals with the same flexibility as the full-season pass.
- Sail up to 4 hours every day
- Rent from the Sonar fleet
- Reservations still required
Already Approved?
Need the booking-page password?
Contact our team with your name and the email used for your WFC account. We’ll confirm your status and help you access booking.
Good to Know
Rental & approval questions
Do ASA or U.S. Sailing certifications replace the WFC Check Out Sail?
No. Outside certifications do not qualify as, or bypass, The WaterFront Center’s Check Out Sail requirement.
What is included in a Check Out Sail?
The Check Out Sail includes a written test and an on-the-water practical evaluation to confirm that a sailor is ready to rent independently and participate safely.
Who can take the Returning Sailor Exam?
Sailors who completed a WFC Check Out Sail within the last two years may be eligible for the $10 Returning Sailor Exam. It is available Monday through Friday from 10:00 AM to 5:00 PM, and results may take up to 72 hours.
Does buying a season pass reserve my sailing dates?
No. Pass holders must reserve each desired rental or group-sailing date through the protected booking page.
Are instructors included with rentals or community sails?
No. Independent rentals, Community Open Sail, and Women on The Water do not include an instructor. If you want instruction, please visit the Adult Sailing Programs page.
Still not sure which option fits?
Our sailing team can confirm your status and guide you to the right program.