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    1. Local experiences/
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    5. Team Racing Sailing Series on Long Island Sound
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    Team Racing Sailing Series on Long Island Sound

    Build team racing skills and strategy on Long Island Sound

    4.5 stars• 62 reviews
    From$53incl. taxes and fees

    Duration

    4 hours

    Ideal For

    4 people

    Highlights

    Practice structured, high-level team racing with individual sailors and club teams. Build skills, strategy, and community on the water.

    • Race in a structured team racing format on Long Island Sound
    • Develop skills, strategy, and on-the-water teamwork
    • Join as an individual sailor or with a club team
    • Meet at The WaterFront Center for your session
    • Plan for a 4-hour program

    Cancellation Policy

    Cancel more than 5 days before for a refund (processing fee not refunded). Within 5 days you may reschedule but no refund. Within 72 hours no refund or reschedule. If the operator cancels due to dangerous weather, you may choose a refund (processing fee not refunded) or reschedule. No-shows get no refund.

    FAQs

    Arrive 15 minutes before your scheduled start time.

    Wear layers appropriate for the forecast. Bring a hat, apply sunblock before you leave land and reapply as needed on the water, and consider bringing a bottle of water.

    If the operator cancels due to imminent and potentially dangerous weather, you can choose to reschedule or get a refund (processing fee not refunded). If the operator delays your start by 30 minutes or more, you can choose to reschedule or get a refund (processing fee not refunded). Delays under 30 minutes are reschedule-only.

    Meeting details

    The WaterFront Center

    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 (650) 414-7338

    Report an issue

    Reference #S76JGC

    Participant

    $53

    Match Racing

    0

    Team Racing Full Boat

    $159

    Full Boat: 1 skipper and 3 crew

    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

    Review summary

    4.5
    Excellent
    62 reviews•Google Maps

    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 5
    5/5

    We booked a special birthday sail on the Christeen for 20 people. Everyone had an amazing time! Our captain and crew were so fun and knowledgeable-sharing fascinating information as we sailed around beautiful Oyster Bay. The front desk staff is also very welcoming and helpful! We plan to book another sail next summer in the evening. Highly recommend!

    Photo of Mari D'Alessandro

    Mari D'Alessandro

    October 6, 2025

    Review 1 of 1
    5/5

    We booked a special birthday sail on the Christeen for 20 people. Everyone had an amazing time! Our captain and crew were so fun and knowledgeable-sharing fascinating information as we sailed around beautiful Oyster Bay. The front desk staff is also very welcoming and helpful! We plan to book another sail next summer in the evening. Highly recommend!

    Photo of Mari D'Alessandro

    Mari D'Alessandro

    October 6, 2025

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