Oyster Bay Two Hour Sailing Experience in Long Island
Long Island, United States

Oyster Bay Two Hour Sailing Experience

Outty Ranking 47 5.0 · 2 traveler reviews2 hoursFrom $625

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September 2026

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Adults

Age 13 and over

2

Children

Age 12 and under

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From, per person$625
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Outty Ranking

47/100

Worth a Look. Our proprietary evaluation. How we score

Traveler rating

5.0/5

Based on 2 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is Oyster Bay Two Hour Sailing Experience worth booking?

Oyster Bay Two Hour Sailing Experience is a 2-hour experience in Long Island, United States, from $625 per person. It scores 47 out of 100 on the Outty Ranking, which we label “Worth a Look, based on a 5/5 rating across 2 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
47 / 100
Rating
5/5 (2)
Duration
2 hours
From
$625 per person

Oyster Bay Harbor's natural beauty affords visitors a temporary respite from bustling city life. Oyster Bay is known for its spectacular sunsets, diverse wildlife, and the impressive estates that line the bay. WINDSWEP

What you get

    About this experience

    Oyster Bay Harbor's natural beauty affords visitors a temporary respite from bustling city life. Oyster Bay is known for its spectacular sunsets, diverse wildlife, and the impressive estates that line the bay. WINDSWEPT is meticulously maintained and equipped with modern amenities. Features include a fully shaded cockpit with an integrated swim platform, Bluetooth stereo, refrigeration, YETI soft cooler, and folding cockpit table. Private sailing charters are perfect settings for celebrating special occasions, enjoying a relaxing day on the water with family and friends, or hosting memorable client events. Those coming from NYC can take the Long Island Railroad (LIRR) from Penn Station to the Oyster Bay stop, which is steps to the marina!

    What's included

    Included

    • Pool floats
    • Stand up paddle board
    • USCG Licensed Captain
    • Fuel
    • Bottled water and ice
    • Bluetooth stereo

    Where it starts and ends

    Meeting point

    Long Island

    Access to the boat is via launch service operated by Oyster Bay Marine Center. The launch ride is 2-3 minutes from the dock. Parking is free.

    Hotel pickup

    No pickup: everyone meets at the start point.

    Ends at

    Access to the boat is via launch service operated by Oyster Bay Marine Center. The launch ride is 2-3 minutes from the dock. Parking is free.

    Before you book

    Cancellation
    For a full refund, cancel at least 24 hours before the scheduled departure time.
    Languages
    en
    Ticket
    Mobile Only
    Runs on
    Every day
    Group size
    Up to 15 travelers per booking
    Operated by
    Windward Sailing Charters

    Know before you go

    • Service animals allowed
    • Public transportation options are available nearby
    • Not recommended for travelers with poor cardiovascular health
    • Suitable for all physical fitness levels

    Photos

    Spacious CabinWalkthrough Transom with Integrated Swim PlatformShaded Cockpit with Seating for 6S/V WINDSWEPT, Jeanneau 36i, Oyster BayWINDSWEPT Under sail!Enjoying another spectacular sunset!

    Traveler reviews

    2 verified traveler reviews for Oyster Bay Two Hour Sailing Experience. Ratings and reviews provided by Viator and Tripadvisor.

    5 star
    2
    4 star
    0
    3 star
    0
    2 star
    0
    1 star
    0
    Sort
    Massimo_P · August 2025

    Sunset Sail

    Went with five friends for a sunset sail. This is an incredible experience! Booking was easy, and we had amazing views of the local area. Capt. Jonathan went above and beyond to make sure everyone was having a great time. Can’t recommend this experience enough!

    Response from the operator: Thank you so much for taking the time to write this review and share your experience! Hope to see everyone again one day!

    via Viator

    A749QTheatherd · July 2025

    Gorgeous Sunset, Beautiful Boat, Great Captain!

    Phenomenal experience. Captain Jonathan kept our group informed and made sure we had a great time. 11/10 would do it again!

    Response from the operator: Thank you for taking the time to write about your experience! So happy to hear that everyone had fun! Until next time!

    via Tripadvisor

    Good to know

    Duration
    2 hours
    Free cancellation
    Up to 24h before
    Minimum age to book
    All ages
    Availability
    Bookable today
    Runs on
    Every day
    Hotel pickup
    No pickup, meet at start point
    Booked in 30 days
    1
    Verdict
    Worth a Look

    Why this scores 47

    The Outty Ranking is a weighted composite. Here is how this experience performed on each component.

    Traveler sentiment (30% weight)68
    Review evidence (18% weight)21
    Booking momentum (14% weight)16
    Value for money (12% weight)0
    Listing quality (10% weight)83
    Local standing (8% weight)56
    Booking flexibility (8% weight)100

    Oyster Bay Two Hour Sailing Experience: questions travelers ask

    Practical detail on this experience, plus the wider planning questions for Long Island.

    How much does Oyster Bay Two Hour Sailing Experience cost?

    +

    Prices start at $625 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Long Island usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.

    How long does Oyster Bay Two Hour Sailing Experience take?

    +

    Plan for about 2 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Long Island is not rushed.

    Is Oyster Bay Two Hour Sailing Experience worth it?

    +

    It holds an Outty Ranking of 47 out of 100, which we label "Worth a Look". That score blends traveler sentiment (5/5 across 2 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Long Island, and how flexible the cancellation terms are.

    Can I cancel or reschedule Oyster Bay Two Hour Sailing Experience?

    +

    Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.

    Is Oyster Bay Two Hour Sailing Experience suitable for kids and families?

    +

    Yes, all ages are welcome. Families should still weigh the 2-hour running time, and strollers are easier on the earlier, quieter departures.

    How far in advance should I book Oyster Bay Two Hour Sailing Experience?

    +

    Around 1 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Long Island can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.

    What should I bring or wear?

    +

    Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Long Island and add a light layer if any part of the 2-hour experience runs outdoors or after sunset.

    Where does Oyster Bay Two Hour Sailing Experience start and how do I get there?

    +

    The exact meeting point and directions are on your voucher once you book, and they sit in central Long Island within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.

    What are the best things to do in Long Island?

    +

    Long Island covers North Fork winery tours, Hamptons beach days, Gold Coast mansion visits and fishing or sailing charters, most reachable as a day trip from Manhattan. On Outty we rank every Long Island experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Private Transfer in Black SUV to or from JFK, LGA, EWR, Skip the Lines Reliable Comfortable and stress free Rides, Black SUV Transfer From or To JFK, LGA, EWR - All Fees Included. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.

    When is the best time to visit Long Island?

    +

    May to October, with harvest tastings peaking in September. Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.

    How many days do you need in Long Island?

    +

    Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.

    Do I book through Outty or through the operator?

    +

    Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.

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