Get hands-on sailing practice in New York Harbor on a Catalina 34
2.5 Hours
Up to 4 people
Hands-on sailing, Instruction
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.
Ages 13+ and up to 4 students per lesson. Tipping the captain 10–20% is customary but not mandatory.
Full refund or reschedule if the operator cancels for bad weather.
Product ID: YNM47B
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.
The marina by Pier 5 in Brooklyn Bridge Park.
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.
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!
Megan Truong
August 9, 2026
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!
Megan Truong
August 9, 2026
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