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    5. /Sail New York Harbor on a Hands-On Sailing Lesson
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    Sail New York Harbor on a Hands-On Sailing Lesson

    Get hands-on sailing practice in New York Harbor on a Catalina 34

    5.0 stars• 265 reviews

    Duration

    2.5 Hours

    Ideal For

    Up to 4 people

    Includes

    Hands-on sailing, Instruction

    Highlights

    Sail around New York Harbor and build practical skills with a hands-on Lesson #2 on a Catalina 34'. With no classroom time, you spend the session practicing on the water.

    • Practice sailing with less instruction for more time at the helm
    • Learn rules of the water and points of sail
    • Handle halyards and sheets to control the sails
    • Practice tacking and jibing with guidance
    • Meet at the marina by Pier 5 in Brooklyn Bridge Park
    • Plan for optional drinks available for purchase onboard

    Things to know

    Ages 13+ and up to 4 students per lesson. Tipping the captain 10–20% is customary but not mandatory.

    Cancellation Policy

    Full refund or reschedule if the operator cancels for bad weather.

    Product ID: YNM47B

    FAQs

    Bring warm clothing for the temperature and wear soft-soled shoes.

    You can buy drinks onboard. A menu is available for purchase, including Champagne, Ros, White Wine, Beer, and Hard Seltzer.

    Tipping the captain 1020% is customary but not mandatory.

    Meeting details

    The marina by Pier 5 in Brooklyn Bridge Park.

    Experience provided by Brooklyn Sail

    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

    Sailing Lesson

    $196.10

    Priced per person • Ages 13+ • Up to 4 students

    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

    5.0
    Excellent
    265 reviews•Google Maps
    251
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    2

    Captains Ian and Andrew have built something genuinely special on the Hudson. Guests consistently rave about how close the boat gets to the Statue of Liberty, and the intimate six-person capacity means you're not fighting for space or shouting over crowds. The sunset sails seem to be a particular favorite, with the Manhattan and Jersey City skylines drawing gasps from locals and tourists alike. Dogs are welcome too, which is a lovely touch. What stands out most across these reviews is how relaxed and professional both captains are. They strike a nice balance between sharing their sailing knowledge and simply letting passengers soak up the experience without feeling lectured. Reviewers note the boat is clean, well-stocked with safety gear, and comfortable enough to move around freely between the front and back. The vibe here is decidedly personal, more private outing than tourist excursion. People come for birthdays, anniversaries, proposals, and casual evenings out, and nearly everyone mentions wanting to return. If you're looking for a genuinely memorable way to experience New York from the water, this is a hard one to talk yourself out of booking.

    What people are saying

    Review 1 of 5
    5/5

    We did a private sunset sail with Andrew to celebrate a birthday and couldn’t recommend it more. As NYC residents, we had so much fun seeing the city in a different way and Andrew made the experience everything we wanted and more. The boat was perfectly sized and comfortable, they have super flexible policies on food/drink (and they’re dog friendly!!), and we had so much fun seeing the sights so up close and personal! We will absolutely be back, thanks Brooklyn Sail!

    Photo of Megan Truong

    Megan Truong

    August 9, 2026

    Review 1 of 1
    5/5

    We did a private sunset sail with Andrew to celebrate a birthday and couldn’t recommend it more. As NYC residents, we had so much fun seeing the city in a different way and Andrew made the experience everything we wanted and more. The boat was perfectly sized and comfortable, they have super flexible policies on food/drink (and they’re dog friendly!!), and we had so much fun seeing the sights so up close and personal! We will absolutely be back, thanks Brooklyn Sail!

    Photo of Megan Truong

    Megan Truong

    August 9, 2026

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