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    1. Local experiences/
    2. Things to do in Oyster Bay…/
    3. Water Activities/
    4. Sailing/
    5. Sunset Cruise in Oyster Bay Harbor
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    Sunset Cruise in Oyster Bay Harbor

    Cruise Oyster Bay Harbor as the sun sets

    4.5 stars• 62 reviews
    From$63/ personincl. taxes and fees

    Duration

    2 hours

    Ideal For

    Up to 24 people

    Includes

    Sunset sail, Crew, Life jackets

    Highlights

    Spend 2 hours cruising around Oyster Bay Harbor on the CHRISTEEN at sunset. Bring friends and family and take in the waterfront views as the sails go up.

    • Explore Oyster Bay Harbor on a sunset cruise
    • Ride aboard the CHRISTEEN with up to 24 passengers
    • Plan a group booking with an 8-passenger minimum
    • Arrive early to check in before departure
    • Know seating is limited when sails are raised or lowered

    Things to know

    No children under 3 years old, and all children must be accompanied by an adult over 18. No animals are allowed aboard. A liability waiver is required before participation.

    Cancellation Policy

    Cancel more than 7 days out for a refund (processing fee not included). Cancel within 7 days but more than 48 hours out: no refund; you may reschedule. Cancel within 48 hours: no refund or reschedule. If you book within 72 hours, you waive your right to a refund.

    FAQs

    Arrive 20 minutes early. The boat leaves promptly at the start time. If you check in later than 15 minutes before departure, you forfeit your spot and refund. If you arrive less than 15 minutes before the sail, you may be able to reschedule (based on availability).

    Bring layers for the forecast, wear a hat, apply sunscreen before you leave, and consider bringing a bottle of water.

    Yes. You must read and sign an Assumption of Risk and Release of Liability Waiver before participating. Waivers are sent with confirmation emails.

    Meeting details

    1 West End Avenue Oyster Bay, NY US 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 #T25VKW

    CHRISTEEN Passenger

    $63.60

    Children under 5 must be accompanied by an adult over the age of 18

    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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