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Hoist the sail on a private sailboat

Set sail on a private sailboat to cruise the waters of Montauk. Join us for a Taste of Sailing boat trip, Sail & Swim, or Sunset Sail. Take the tiller or sit back and relax, our captains will show you the ropes. Learn to sail with us, Sail Montauk is a Certified Sailing School with the American Sailing Association. We offer private lessons, certification courses, and private kid's lessons. Already know how to sail? Check out our bareboat rentals. 

Sail Montauk is an American Sailing Association affiliate. Our captains are US Coast Guard Licensed and experienced sailing instructors.



Sailing is a recreational and social activity, and in our own small way we hope our actions can help reduce the spread of the virus. 

We will be resuming sails on June 27th, and are currently accepting private bookings for limited activities. We've postponed all group classes, Junior Sailing Program, and Flotilla Boat Parties until 2021; but will still be offering Private Lessons, Private Charters, and Bareboat Rentals.


Due to the complications of social distancing protocols and concern for the health and safety of our instructors, staff, and sailors; we will be offering limited activities for the 2020 season. We are currently accepting bookings for Private Lessons, Private Charters, and Bareboat Rentals.


We will only be accepting "QuaranTEAMS" aboard our private trips and lessons, and limiting the capacity to 3 guests on lessons and charters. Exceptions of 4 will be made if there are children in your party. Bareboat rentals will still be allowed up to 6 guests. 


To ensure the safety of all, our Captains will be wearing masks and we're requiring the same for participants. We strongly encourage you to bring your own, but we'll have masks available if needed. Boats will be wiped down and sanitized between each trip and hand sanitizers will be kept aboard for your convenience. 


Sail Montauk will be operating at Westlake Marina this summer, but will return to Gurney's Star Island in 2021.

Since our Junior Sailing Camp has been postponed, we're offering a special rate for kids private lessons this summer. You'll have the option to book 1 lesson, or multiple lessons at a discounted rate. This is a good option for quanTEAMS and will include many of the regular sail camp activities.

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Sailing from: Gurney's Star Island Resort & Marina

32 Star Island rd. Slip 412 Montauk, NY 11954  |  Tel. 631-522-5183

© 2020 by Sail Montauk