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    1. Local experiences
    2. /Things to do in Oyster Bay…
    3. /Water Activities
    4. /Sailing
    5. /Community Sailing Session in Oyster Bay
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    Community Sailing Session in Oyster Bay

    Build your sailing skills with instructor-guided time on Oyster Bay Harbor

    4.5 stars• 62 reviews
    From$90/ personincl. taxes and fees

    Duration

    2 hrs weekdays; 3 hrs weekends

    Includes

    On-water instructor, sailing time

    Highlights

    Practice your sailing skills on Oyster Bay Harbor alongside fellow sailors. An on-water instructor supervises each session, offering answers and coaching as you sail.
    • Practice sailing techniques with guidance from an on-water instructor
    • Meet fellow sailors during a shared harbor session
    • Explore Oyster Bay Harbor under sail
    • Refine your skills with hands-on coaching and answers to questions

    Know before you go

    • Ages 18+ only
    • Requires prior sailing experience and a passed Check-out Sail/Returners test
    • Arrive 15 minutes before your scheduled session
    • Bring weather-appropriate layers, a hat, sunblock, and water

    Cancellation Policy

    Cancel more than 5 days before for a refund excluding the processing fee. Cancel 3–5 days before to reschedule only. No refund or rescheduling within 72 hours. Weather cancellations or delays of 30+ minutes allow a refund excluding the processing fee or rescheduling; shorter delays allow rescheduling only. No-shows receive no refund or rescheduling.

    FAQs

    Prior sailing experience and a passed Check-out Sail/Returners test are required.

    Bring weather-appropriate layers, a hat, sunblock, and water.

    Meeting details

    1 West End Avenue, Oyster Bay, NY 11771

    Experience provided by The WaterFront Center
    Experience provided by The WaterFront Center

    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 #63EUBT

    Participant

    $90.10

    0

    Why book through Greetwell?

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    • Free Cancellation Available

      Most experiences can be cancelled for a full refund

    Discover what we've curated for you

    Review summary

    4.5
    Excellent
    62 reviews•Google Maps
    71
    8
    0
    1
    12

    The sailing experiences here get rave reviews, particularly aboard the historic Christeen. Guests consistently praise the knowledgeable captains and crew who share fascinating stories while navigating Oyster Bay's waters. The sunset sails seem especially popular, and many appreciate the hands-on experience of helping raise the sails on a vessel with such remarkable history. Beyond sailing, the kayak rentals and wildlife tours are winners too, with naturalists like Lauren earning special mentions for their expertise in spotting ospreys and other local wildlife. There's a concerning pattern worth noting though. Multiple groups report last-minute cancellations, sometimes just an hour before scheduled departures, with birthday celebrations being particularly affected. Several reviewers describe frustrating interactions with staff during these situations and mention inconsistent explanations. That said, the majority of visitors have smooth, memorable experiences with friendly, helpful staff both on the water and at the front desk. The kayaking, sailing lessons, and scenic tours consistently deliver when things go as planned, making this a solid choice if you stay flexible with your schedule.

    What people are saying

    Review 1 of 4
    5/5

    Booked 2 single kayaks for 1.5 hours. Easy to book, good price, and we had a very nice time!

    Photo of Sivan Ertel

    Sivan Ertel

    July 6, 2026

    Review 1 of 1
    5/5

    Booked 2 single kayaks for 1.5 hours. Easy to book, good price, and we had a very nice time!

    Photo of Sivan Ertel

    Sivan Ertel

    July 6, 2026

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