Sailing School 

We welcome sailors of every level - from kids stepping into a boat for the first time to those already comfortable on the water and more. Instructors keep a close eye on each child’s progress and adjust groups, so everyone learns at a pace that feels right.

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Safety comes first, but we also know sailing should be fun. Alongside our hands‑on instruction, we weave in a variety of activities that help kids discover the Chesapeake Bay and practice a variety of sailing skills. By keeping learning fresh and exciting, from exploring local wildlife to mastering new techniques, we build the foundation for confidence on the water and nurture a love of sailing and the Bay that will last well beyond the summer.

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Each session wraps up with something special.  It might be a sail out to Treasure Island on Pirate Day for lunch and a treasure hunt, Sailing Olympics, or a picnic at Round Bay where we’ve spotted hatching horseshoe crabs in the past. These adventures give kids a chance to explore, laugh with friends, and build memories that last long after summer ends.

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Skill Levels & Boats

While it's helpful if you can designate their level, don't worry too much if you're not sure—we'll continuously assess them and place them in the appropriate group.

• Beginner: For new sailors learning the basics in Optis or 420s.

• Intermediate: For kids who can sail independently and want to build confidence and seamanship skills.

• Advanced/Racer: For those ready to explore racing techniques and tactics. Racing is optional, but opportunities are available for anyone who wants to give it a try.

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We offer our basic lessons in Optis, Lasers (ILCA), and 420s. If you're not sure what boat your young sailor should be sailing, please check out our What boat should my kid sail?

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NEW in 2026:

We have three new classes for our more experienced sailors: Fleet Exploration, 29er Clinics, and a High School Sailing Jump Start Week. For more details, please check out our Clinic and Off-Season Program Page.

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Please email the Director at Education@westriversc.com if you have any questions.

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If you are in need of extended care services for our summer program,

we should be able to assist with that.

Please contact the Director at education @ westriversc.com.

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