Southernmost Youth Regatta - January 16-18, 2026. Click HERE to reigster!
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Events

KWSC Intro

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

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.