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    1. Local experiences
    2. /Things to do in Saint Helena Island…
    3. /Water Activities
    4. /Sailing
    5. /3.5-Hour Sailing Lesson in Saint Helena Island
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    3.5-Hour Sailing Lesson in Saint Helena Island

    Take the helm with a private, customizable keelboat sailing lesson

    5.0 stars• 39 reviews
    From$477incl. taxes and fees

    Duration

    3.5 hrs

    Ideal For

    Up to 6 people

    Includes

    Private sailing lesson, water

    Highlights

    Learn the fundamentals of keelboat sailing aboard a Catalina 275 Sport, whether you are sailing for the first time or building on existing skills. Shape your time on the water around the sailing skills and activities that interest you.

    • Practice sailing skills with a private lesson aboard a Catalina 275 Sport
    • Customize your time on the water around your learning goals
    • Explore options such as swimming at a sandbar
    • Look for monkeys on Monkey Island without wildlife guarantees
    • Bring food and drinks in a soft-sided cooler

    What's Included

    • Complimentary water
    • Access to the below-deck cabin

    Important details

    • Ages 12+ only to sail alone
    • Leave glass containers and red liquids, including red wine, ashore
    • Do not use spray sunscreen on board
    • Expect charters to continue through brief thunderstorms; a below-deck cabin is available during rain or lightning
    • Optional captain and crew gratuity is not included in the listed price

    Cancellation Policy

    Free cancellation with at least 24 hours' notice. Full refund if the operator cancels due to weather or other unforeseen circumstances. No-shows are charged the full price.

    FAQs

    Dress for current weather conditions, bring needed sun protection, and wear shoes and clothing that can get wet. Bring an extra layer in fall, winter, or spring, when it can be cooler on the water.

    Yes. Use the bathroom below deck to change into or out of swim attire, and bring a beach bag or backpack with supplies such as towels.

    Meeting details

    3 Dulamobluff, Saint Helena Island, SC, US

    Experience provided by Otter Sailing Adventures LLC

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text 1-877-GREET-WELL

    Report an issue

    Reference #CKU73N

    Private Charter

    $477

    Select 1 charter for up to 6 People

    0

    Why book through Greetwell?

    • No Added Fees

      No booking or service fees, ever

    • Concierge Support Included

      Real humans ready to help with timing, questions, or special requests

    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    What people are saying

    Review 1 of 5
    5/5

    My wife, daughter, and I enjoyed going out sailing with Barry on his sailboat during our vacation to Beaufort. Barry is a genuine down to earth guy with whom I really enjoyed talking with. I’ve never been on a sailboat, and wanted to learn the basics of how to sail, so Barry put together a beginners lesson. I highly recommend looking up Barry with Otter Sailing Adventures if interested in sailing or looking to go out on a private charter.

    Photo of John MacKorell

    John MacKorell

    July 18, 2026

    Review 1 of 1
    5/5

    My wife, daughter, and I enjoyed going out sailing with Barry on his sailboat during our vacation to Beaufort. Barry is a genuine down to earth guy with whom I really enjoyed talking with. I’ve never been on a sailboat, and wanted to learn the basics of how to sail, so Barry put together a beginners lesson. I highly recommend looking up Barry with Otter Sailing Adventures if interested in sailing or looking to go out on a private charter.

    Photo of John MacKorell

    John MacKorell

    July 18, 2026

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