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 25, 2026
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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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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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Moonlight Regatta
Come race with us on the full moon! 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
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Homeschool Sailing
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Homeschool Sailing
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Sailing 101 & 102 (Opti Optional)
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- October 27, 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 28, 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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Sigsbee Sailing Program
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Racing 101 or Adventure Sailing Program
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- October 29, 2026
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Somerset
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Development Team or Keelboat 101
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- October 30, 2026
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Montessori Sailing Program
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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 31, 2026
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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
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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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- November 2, 2026
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Homeschool Sailing
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Homeschool Sailing
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Sailing 101 & 102 (Opti Optional)
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- November 3, 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.
-
Somerset
-
Little Skippers (Opti Optional)
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- November 4, 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.
-
Sigsbee Sailing Program
-
Racing 101 or Adventure Sailing Program
-
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- November 5, 2026
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Somerset
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Development Team or Keelboat 101
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- November 6, 2026
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CFK Academy Volunteers
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Montessori Sailing Program
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KWCSC Race Team
**Pre-registration required, and on an invite-only basis*
Visit our website for more information on our Youth Programs. -
First Friday Potluck & Guest Speaker Series
Join us for our monthly social potluck at the Key West Community Sailing Center!
This event is open to all members, friends, and anyone interested in becoming part of our sailing community. Bring a dish or drinks to share, enjoy good company, and hear from this month’s featured speaker.
See our Facebook page for additional details and to let us know what dish you will be bringing.
The evening begins at 6:00 PM, with the speaker’s presentation starting at 6:30 PM.
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- November 7, 2026
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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.
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Members Sailing Clinic: Hobie 16
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 November, we will be learning how to rig and sail the Hobie 16.
The Hobie 16 is a powerful catamaran built entirely for speed, with maximum speeds of 20-24 knots. This is a widely popular racing boat that delivers a shot-of-adrenaline that our other fleets just cannot offer. KWCSC owns one Hobie 16 so come excited, but also patient. We hope to ensure all participants have a chance to learn and have fun.
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- November 8, 2026
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-
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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- November 9, 2026
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Homeschool Sailing
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Homeschool Sailing
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Sailing 101 & 102 (Opti Optional)
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- November 10, 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.
-
Somerset
-
Little Skippers (Opti Optional)
-
- November 11, 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.
-
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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- November 12, 2026
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Somerset
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Development Team or Keelboat 101
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- November 13, 2026
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CFK Academy Volunteers
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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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- November 14, 2026
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Member's Flotilla
This staff-led sailing adventure takes us beyond our usual sailing area to a new destination for a full day of sailing, swimming, relaxing, and enjoying the water together. Pack a lunch, grab your favorite people, and get geared up for a day on the water. Destination determined by conditions. Options include: Mud Keys, Jewfish Basin Sandbars, Channel Key, Cayo Aqua, Bay Keys, etc. Boats are first-come-first-serve. Join us on WhatsApp to find a Skipper or Crew.
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- November 15, 2026
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Yoga at KWCSC
Join us for an open-air yoga class at the Key West Community Sailing Center! Guests are welcome to stay for our Sunday Open Sailing Class following yoga, from 10 AM - 12 PM.
Bring your own mat!
This event is open to all members, friends, and anyone interested in becoming part of our sailing community.
This is a donation-based class with a $10 minimum, all proceeds benefit KWCSC. Register here: https://keywestsailingcenter.app.neoncrm.com/forms/yoga-at-kwcsc-registration
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Key West Artisan Market at Higgs Beach
Local artisans and authors, live music, and fresh food. Stop by our table and say, "Hello!" -
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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- November 16, 2026
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-
Homeschool Sailing
-
Homeschool Sailing
-
Sailing 101 & 102 (Opti Optional)
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- November 17, 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 18, 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 19, 2026
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-
Somerset
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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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- November 20, 2026
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CFK Academy Volunteers
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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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- November 21, 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: Hobie 16
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 November, we will be learning how to rig and sail the Hobie 16.
The Hobie 16 is a powerful catamaran built entirely for speed, with maximum speeds of 20-24 knots. This is a widely popular racing boat that delivers a shot-of-adrenaline that our other fleets just cannot offer. KWCSC owns one Hobie 16 so come excited, but also patient. We hope to ensure all participants have a chance to learn and have fun.
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- November 22, 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 23, 2026
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-
-
Moonlight Regatta
Come race with us on the full moon! 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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- November 24, 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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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.