Events
From strictly social to sporty competition, we offer sailing-oriented activities for all ages. These include festive regattas, weekly racing, our annual Round the Island Race, and much more. Check out our calendar and events listings for upcoming fun.
Calendar
- October 6, 2026
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Locals Open Sailing Class (Free)
**No registration required**
Open Sailing Class - men and women welcome. Join with members and others for group instruction and on-the-water sailing instruction.
Led by trained instructor.
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Somerset
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Little Skippers (Opti Optional)
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- October 7, 2026
-
-
Locals Open Sailing Class (Free)
**No registration required**
Open Sailing Class - men and women welcome. Join with members and others for group instruction and on-the-water sailing instruction.
Led by trained instructor.
-
Sigsbee Sailing Program
-
Racing 101 or Adventure Sailing Program
-
-
- October 8, 2026
-
-
Somerset
-
Development Team or Keelboat 101
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- October 9, 2026
-
-
CFK Academy Volunteers
-
Montessori Sailing Program
-
KWCSC Race Team
**Pre-registration required, and on an invite-only basis*
Visit our website for more information on our Youth Programs.
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- October 10, 2026
-
-
Women's Open Sailing Class (Free)
**No registration required**
Open Sailing Class - women welcome. Join with members and others for group instruction and on-the-water sailing instruction.
Led by trained instructor.
-
Members Sailing Clinic: Lasers
This free Members class has a simple goal: help you learn new boats, so you can get checked out on a new fleet.
Over the course of the month, we will focus on entry-level skills (rigging, leaving and returning to the dock, and tacking & gybing), and move into intermediate skills as participants progress and conditions allow.
For the month of October, we will be learning how to rig and sail Lasers.
The Laser is a popular racing sailboat that has been an Olympic-class fleet since 1996. Officially named the ILCA Dinghy, the Laser has 3 rig-sizes: ILCA 4 (for sailors 110 - 125 pounds), 6 (for sailors 145 - 160 pounds), and 7 (for sailors 175 - 200+ pounds). This is an excellent boat for intermediate sailors who are looking to improve their boat handling skills, but it does require some strength, flexibility, and speed.
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- October 11, 2026
-
-
Open Sailing Class (Free)
**No registration required**
Open Sailing Class - men and women welcome. Join with members and others for group instruction and on-the-water sailing instruction.
Led by trained instructor.
-
Member Racing
**No registration required**
Members and their crew come together for fun and friendly competition. Youth Sailors from the KWCSC Race Team and Development Team encouraged to participate.
Center boats available on first-come, first-served basis. Private boats welcome.
1 pm - Skippers meeting
2 pm - First start
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- October 12, 2026
-
-
Homeschool Sailing
-
Homeschool Sailing
-
Sailing 101 & 102 (Opti Optional)
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- October 13, 2026
-
-
Locals Open Sailing Class (Free)
**No registration required**
Open Sailing Class - men and women welcome. Join with members and others for group instruction and on-the-water sailing instruction.
Led by trained instructor.
-
Somerset
-
Little Skippers (Opti Optional)
-
- October 14, 2026
-
-
Locals Open Sailing Class (Free)
**No registration required**
Open Sailing Class - men and women welcome. Join with members and others for group instruction and on-the-water sailing instruction.
Led by trained instructor.
-
Sigsbee Sailing Program
-
Racing 101 or Adventure Sailing Program
-
Pizza Night
**Checked-Out Members Only** Sail during Golden Hour and share some pizza with friends!
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- October 15, 2026
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-
Somerset
-
Development Team or Keelboat 101
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Walk on White
A monthly art walk since 1999, Walk on White is now a celebration of more than 20 local business in the White Street Gallery District! Stop by our table and say, "Hello!"
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- October 16, 2026
-
-
CFK Academy Volunteers
-
Montessori Sailing Program
-
KWCSC Race Team
**Pre-registration required, and on an invite-only basis*
Visit our website for more information on our Youth Programs.
-
- October 17, 2026
-
-
Women's Open Sailing Class (Free)
**No registration required**
Open Sailing Class - women welcome. Join with members and others for group instruction and on-the-water sailing instruction.
Led by trained instructor.
-
Members Sailing Clinic: Lasers
This free Members class has a simple goal: help you learn new boats, so you can get checked out on a new fleet.
Over the course of the month, we will focus on entry-level skills (rigging, leaving and returning to the dock, and tacking & gybing), and move into intermediate skills as participants progress and conditions allow.
For the month of October, we will be learning how to rig and sail Lasers.
The Laser is a popular racing sailboat that has been an Olympic-class fleet since 1996. Officially named the ILCA Dinghy, the Laser has 3 rig-sizes: ILCA 4 (for sailors 110 - 125 pounds), 6 (for sailors 145 - 160 pounds), and 7 (for sailors 175 - 200+ pounds). This is an excellent boat for intermediate sailors who are looking to improve their boat handling skills, but it does require some strength, flexibility, and speed.
-
- October 18, 2026
-
-
Open Sailing Class (Free)
**No registration required**
Open Sailing Class - men and women welcome. Join with members and others for group instruction and on-the-water sailing instruction.
Led by trained instructor.
-
Member Racing
**No registration required**
Members and their crew come together for fun and friendly competition. Youth Sailors from the KWCSC Race Team and Development Team encouraged to participate.
Center boats available on first-come, first-served basis. Private boats welcome.
1 pm - Skippers meeting
2 pm - First start
-
- October 19, 2026
-
-
Homeschool Sailing
-
-
Homeschool Sailing
-
Sailing 101 & 102 (Opti Optional)
-
- October 20, 2026
-
-
Locals Open Sailing Class (Free)
**No registration required**
Open Sailing Class - men and women welcome. Join with members and others for group instruction and on-the-water sailing instruction.
Led by trained instructor.
-
Somerset
-
Little Skippers (Opti Optional)
-
- October 21, 2026
-
-
Locals Open Sailing Class (Free)
**No registration required**
Open Sailing Class - men and women welcome. Join with members and others for group instruction and on-the-water sailing instruction.
Led by trained instructor.
-
Sigsbee Sailing Program
-
Racing 101 or Adventure Sailing Program
-
- October 22, 2026
-
-
Somerset
-
Development Team or Keelboat 101
-
- October 23, 2026
-
-
CFK Academy Volunteers
-
Montessori Sailing Program
-
KWCSC Race Team
**Pre-registration required, and on an invite-only basis*
Visit our website for more information on our Youth Programs.
-
- October 24, 2026
-
-
Women's Open Sailing Class (Free)
**No registration required**
Open Sailing Class - women welcome. Join with members and others for group instruction and on-the-water sailing instruction.
Led by trained instructor.
-
Members Sailing Clinic: Lasers
This free Members class has a simple goal: help you learn new boats, so you can get checked out on a new fleet.
Over the course of the month, we will focus on entry-level skills (rigging, leaving and returning to the dock, and tacking & gybing), and move into intermediate skills as participants progress and conditions allow.
For the month of October, we will be learning how to rig and sail Lasers.
The Laser is a popular racing sailboat that has been an Olympic-class fleet since 1996. Officially named the ILCA Dinghy, the Laser has 3 rig-sizes: ILCA 4 (for sailors 110 - 125 pounds), 6 (for sailors 145 - 160 pounds), and 7 (for sailors 175 - 200+ pounds). This is an excellent boat for intermediate sailors who are looking to improve their boat handling skills, but it does require some strength, flexibility, and speed.
-
- October 25, 2026
-
-
Open Sailing Class (Free)
**No registration required**
Open Sailing Class - men and women welcome. Join with members and others for group instruction and on-the-water sailing instruction.
Led by trained instructor.
-
Member Racing
**No registration required**
Members and their crew come together for fun and friendly competition. Youth Sailors from the KWCSC Race Team and Development Team encouraged to participate.
Center boats available on first-come, first-served basis. Private boats welcome.
1 pm - Skippers meeting
2 pm - First start
-
Moonlight Regatta
**Checked-Out Members Only** Come race with us on the full moon! Sign-in (and share your emergency contact information) when you arrive. Boats are first-come-first serve. We will provide the essential lights, but you can provide the fun ones! Please no glow-sticks. 6:00 - Skipper's Meeting 6:30 - First Warning Signal No warning signals after 8:00 Email Savannah Welton at programdirector@kwcsc.org with questions.
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- October 26, 2026
-
-
Homeschool Sailing
-
Homeschool Sailing
-
Sailing 101 & 102 (Opti Optional)
-
- October 27, 2026
-
-
Locals Open Sailing Class (Free)
**No registration required**
Open Sailing Class - men and women welcome. Join with members and others for group instruction and on-the-water sailing instruction.
Led by trained instructor.
-
Somerset
-
Little Skippers (Opti Optional)
-
- October 28, 2026
-
-
Locals Open Sailing Class (Free)
**No registration required**
Open Sailing Class - men and women welcome. Join with members and others for group instruction and on-the-water sailing instruction.
Led by trained instructor.
-
Sigsbee Sailing Program
-
Racing 101 or Adventure Sailing Program
-
- October 29, 2026
-
-
Somerset
-
Development Team or Keelboat 101
-
- October 30, 2026
-
-
-
CFK Academy Volunteers
-
Montessori Sailing Program
-
KWCSC Race Team
**Pre-registration required, and on an invite-only basis*
Visit our website for more information on our Youth Programs.
-
- October 31, 2026
-
-
-
7th Annual Halloween Regatta
This spooktacular event will consist of sailing races, a costume competition, games and raffles. Guaranteed to be fun for the entire family, costumes are highly encouraged!
Open to Members and Non-Members
For further details, including a full schedule, see the Notice of Race HERE.
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- November 1, 2026
-
-
Open Sailing Class (Free)
**No registration required**
Open Sailing Class - men and women welcome. Join with members and others for group instruction and on-the-water sailing instruction.
Led by trained instructor.
-
Member Racing
**No registration required**
Members and their crew come together for fun and friendly competition. Youth Sailors from the KWCSC Race Team and Development Team encouraged to participate.
Center boats available on first-come, first-served basis. Private boats welcome.
1 pm - Skippers meeting
2 pm - First start
-
- November 2, 2026
-
-
-
Homeschool Sailing
-
Homeschool Sailing
-
Sailing 101 & 102 (Opti Optional)
-
- November 3, 2026
-
-
Locals Open Sailing Class (Free)
**No registration required**
Open Sailing Class - men and women welcome. Join with members and others for group instruction and on-the-water sailing instruction.
Led by trained instructor.
-
Somerset
-
Little Skippers (Opti Optional)
-
- November 4, 2026
-
-
Locals Open Sailing Class (Free)
**No registration required**
Open Sailing Class - men and women welcome. Join with members and others for group instruction and on-the-water sailing instruction.
Led by trained instructor.
-
Sigsbee Sailing Program
-
Racing 101 or Adventure Sailing Program
-
-
- November 5, 2026
-
-
Somerset
-
Development Team or Keelboat 101
-
Featured Events
Sunday afternoon racing – Weekly friendly competition with Skippers Meeting at 1 pm to announce course and other details. Local residents/non-members are invited to participate as crew, space permitting.
Regattas – Periodic special series of fun and competitive races. Our popular Halloween Regatta is an annual event. For other regattas, we have invited neighboring sailing centers to participate and our sailors also travel to nearby sister organizations’ regattas.
Center socials – We gather at our beautiful waterfront pavilion and beach for comraderie at planned and ad-hoc social times.
Round the Island Race – A longstanding annual spring tradition that involves a sail around the island of Key West. It starts and finishes at the Sailing Center. Members and visitors are welcome, using Center and private boats. An awards ceremony is held at the conclusion of this fun adventure.
Community partnerships – The Center partners with local Key West organizations and others through supportive activities. “Come About Boating Adventures” are offered, when Center volunteers take clients of M.A.R.C. House (pictured here) out on the water. We have also hosted traveling programs such as SailFuture’s Defy the Odds student sailing and study experience.
Watch our Calendar HERE for sailing activities, socials and other events.
Summer Camp
Community partnerships – The Center partners with local Key West organizations and others through supportive activities. “Come About Boating Adventures” are offered, when Center volunteers take clients of M.A.R.C. House (pictured here) out on the water. We have also hosted traveling programs such as SailFuture’s Defy the Odds student sailing and study experience.
Watch our Calendar HERE for sailing activities, socials and other events.