Come Sail Montauk With Us!

Your Boat!

Your Captain!

Your Tunes!

Your Experience! 

Join us during the winter months for a live aboard sailing vacation in the beautiful Caribbean. 

Island hop to a new paradise destination each day aboard a luxury sailboat.

​

Learn to sail at your own pace with private instruction or check out one of our classes for adults or junior sailors. Sail Montauk is an American Sailing Association certified sailing school. The waters of the Hamptons are the perfect place to learn to sail. Cruise Montauk with us!

Not your typical hamptons boat ride! Plan the perfect private sailboat tour in Montauk. Set sail with a licensed captain to show you the ropes, or just sit back and relax on our private boats. Our charters are "hands on" do as much or as little as you like. Perfect for bachelorette parties, families, couples, and groups.

Join us in the evening for a Private Montauk Sunset Sail. All boats have coolers with complimentary ice & waters. Feel free to BYOB. Cups and bottle openers are provided. Connect to our bluetooth speaker for your custom playlist. Our Montauk sunset cruise is our most popular, so be sure to book soon! 

Step off the dock onto one of private sailboats for an exhilarating sail on the waters of Montauk.

About Sail Montauk

Set sail on a private sailboat cruise on 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. For big groups, book a Race Day or Flotilla Boat Party (water guns included). Learn to sail with us, Sail Montauk is a Certified Sailing School with the American Sailing Association. We offer private lessons, certification courses, and a kids sail camp. Already know how to sail? Check out our bareboat rentals. Come SAIL MONTAUK with us!

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