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    Otter Sailing Adventures LLC

    Otter Sailing Adventures LLC

    5.0 • 39 reviews
    Saint Helena Island, SC

    Otter Sailing Adventures offers a relaxed, memorable way to experience Beaufort’s Lowcountry from the water. Locally owned and operated on Saint Helena Island, each private charter is captained by owner Barry Gupton, a licensed US...

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    Book Otter Sailing Adventures LLC

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    3.5-Hour Sailing Lesson in Saint Helena Island

    Take the helm with a private, customizable keelboat sailing lesson

    $477
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    Dolphin & Monkey Sailing Cruise on Saint Helena Island

    Sail quiet Lowcountry waterways while looking for dolphins and Morgan Island monkeys

    $371
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    Saint Helena Island Sunset Sailing Charter

    Private sunset sailing with room below deck for passing weather

    $397.50
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    2.5-Hour Sailing Charter on Saint Helena Sound

    Private sailing with dolphin sightings on Saint Helena Sound

    $371

    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