Set sail on a private sailboat on the waters of Montauk. Join us for a Taste of Sailing 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!