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Sail Montauk

Sail Montauk - Unforgettable Sailing in The Hamptons

Dreaming of sailing in The Hamptons during your stay? The Montauk Yacht Club and Sail Montauk have partnered to offer private sailing charters that depart from our own Montauk marina. Our sailing trips are hands on, allowing you to do as much or as little as you please. Take the tiller or sit back and relax with a cool beverage in hand. Enjoy a romantic sunset sail for two, or register for a private lesson and learn how to handle a Catalina 22. We also offer festive Flotilla Boat Parties ideal for large families, corporate events and even bachelorette parties.

Sail Montauk is located at slip 412 in the Montauk Yacht Club Marina. For more information about sailing in Montauk, call us at 631.522.5183 or visit www.sailmontauk.com.

Taste of Sailing - Sail with our Captain and experience what it's like to be crew on a sloop. Hoist the sails, trim the sheets, and take the tiller, or just relax and let our crew do all the work during this scenic two-hour sail.

  • Available 11am or 2pm
  • From $170 per boat (price includes first two passengers)
  • $60 each additional person, $40 each additional child under 12

Sail & Swim - Enjoy a ‘Taste of Sailing’ with some additional swim time, and get the best of both worlds during this three-hour excursion. Midway through your private sail, we'll tie off for a swim and some water games, or relax on the boat with your picnic lunch. Water guns and pool noodles are kept on board and we encourage cannonballs, so make a splash! 

  • Available 10am or 2pm
  • From $255 per boat (price includes 1st two passengers)
  • $60 each additional person, $40 each additional child under 12 years old

Private Lessons  - Ideal for beginners or as a refresher course, you will learn aboard a Catalina 22 sailboat which is both comfortable and easy to handle.

Basic Sailing Courses  - Learn to sail with our Basic Sailing Course, no experience necessary. Students will gain knowledge of basic sailing terminology, parts and functions of a sailboat, points of sail, safety and navigation rules, knot tying and much more.

Junior Sailing Program - Designed for kids ages 10-16, our summer sailing program covers the fundamentals of Basic Sailing, and students will get to participate in on-the-water games and racing.

Two Week Sessions l 9:30am to 12:30pm - $590 per student

Session 1: June 30 - July 11
Session 2: July 14 - July 25
Session 3: August 4 - August 15

Sunset Sail  - Enjoy the beautiful Montauk sunset on your very own private sail. Nibble on snacks, listen to music and sip champagne with your sweetheart.

Flotilla Boat Parties  - Designed for large groups, this excursion involves multiple boats that sail alongside each other flotilla style. Raft up for picnic parties and swimming, experience a head-to-head race or play cat and mouse with water guns and gain bragging rights for the season.  Perfect for bachelorette parties, family reunions, corporate events, and team building workshops.

  • Available 10am or 2pm
  • From $255 per boat (price includes first two passengers)
  • $60 per additional person, $40 for guests under 12

18% gratuity for your captains will be added to your total.

Bareboat Rentals - Already know how to sail?  Rent a Catalina 22 sailboat for the day and create timeless memories as you cruise around Montauk.