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    1. Local experiences/
    2. Oyster Bay, NY/
    3. Water Activities/
    4. Sailing/
    5. Sunset Cruise Aboard The Christeen in Oyster Bay

    The very best experiences curated by local experts

    Best local prices
    Flexible cancellations
    Private & secure
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    Sunset Cruise Aboard The Christeen in Oyster Bay

    Sail Oyster Bay Harbor at golden hour and share unforgettable sunset views with up to 24 fellow passengers.

    From$55/ person

    Duration

    2 hrs

    Ideal For

    Up to 24 people

    Includes

    Sunset sail, Crew, Life jackets

    Highlights

    Board the historic Christeen and glide across Oyster Bay Harbor as the sky shifts into vibrant sunset hues. Relax with friends and family during this two-hour sail.

    1. Watch the sun dip below Long Island's coastline
    2. Enjoy smooth sailing aboard a classic oyster sloop
    3. Capture photo-worthy views of shoreline and wildlife
    4. Learn about Oyster Bay's maritime heritage from crew
    5. Bring layers, hat, sunscreen and water for comfort

    What's Included

    1. Two-hour sunset sail
    2. USCG-certified captain and crew
    3. Life jackets

    Things to know

    Children under 3 are not permitted; all minors must sail with an adult 18 or older. The Christeen carries up to 24 guests and requires a minimum of eight confirmed passengers 48 hours before departure.

    Cancellation policy

    Cancel more than seven days before departure for a refund minus processing fees. Cancel between seven and two days in advance to reschedule only; no refunds. Cancellations within 48 hours, bookings made within 72 hours, or no-shows receive no refund. Weather-related cancellations are decided by The WaterFront Center; you may reschedule or receive a refund minus processing fees.

    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

    Reference #T25VKW

    CHRISTEEN Passenger

    $55

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

    1

    Handpicked for you, so you can book with confidence

    • Best local prices

    • Flexible cancellation

    • Private and secure

    Each booking directly supports small businesses in our community.

    4.4 stars• 91 reviews

    Review summary

    4.4
    Very Good
    91 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

    this was so cool and so much fun. its truly amazing when you realize you are standing on a boat that was built at the same time of the shootout at the OK Corall. the staff were knowledgeable and friendly. the weather was great. we all helped raise the sails. We are going to bring friends to do it again. We really really loved it!

    Photo of Ryan Vasey

    Ryan Vasey

    July 28, 2025

    Review 1 of 1
    5/5

    this was so cool and so much fun. its truly amazing when you realize you are standing on a boat that was built at the same time of the shootout at the OK Corall. the staff were knowledgeable and friendly. the weather was great. we all helped raise the sails. We are going to bring friends to do it again. We really really loved it!

    Photo of Ryan Vasey

    Ryan Vasey

    July 28, 2025

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