Sail Montauk

Sail Montauk

Come Sail Montauk with us!  Sunset Sails, Boat Parties,
Sailing Lessons, Water Gun Fights.

The Montauk Yacht Club Resort & Marina and Sail Montauk have partnered
 to offer private sailing charters that depart from our own Montauk marina. Sail Montauk is a charter company and sailing school that offers private sailing trips and sailing lessons.  It's an accredited sailing school with the American Sailing Association and has the largest sailing fleet in Montauk.  All instructors hold a US Coast Guard Captains License.

All trips are private and hands on, do as much as or as little as you like.  Sail with our captain and experience what it is like to crew on a sloop.  Hoist the sails, trim the sheets, take the tiller, or just sit back and relax with a cool beverage in hand.

No experience necessary.
Feel Free to BYOB or bring snacks.
Coolers with complimentary ice, waters, and soft drinks.
Bluetooth speakers for a custom playlist.
Boats equipped with pool noodles and water guns.

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

Taste of Sailing  (2 hours) 11am or 2pm
 $220 includes first two guests
$60 for each additional adult, $40 for each additional child under 12
Sunset Sail (2 hours) 6pm
 $220 includes first two guests
$60 for each additional adult, $40 for each additional child under 12

Sail & Swim (3 hours) 10am or 2pm
 $290 includes 1st two guests
$60 for each additional person, $40 each additional child under 12
Flotilla Boat Parties (3 hours) 10am or 2pm
Designed for larger groups, this excursion involves multiple boats that sail along side each other flotilla style.  Raft up for picnic parties and swimming, experience a head-to-head race or play cat mouse with water guns and gain bragging rights for the season.  Perfect for bachelorette parties, family reunions, corporate outings, and team building workshops.
For pricing, contact us or visit
Learn to Sail -
ASA Basic Keelboat 101 Course: Starting at $525
2 or 3 hour Private Sailing Lessons: Starting at $110 per hour
Bareboat Rentals 
Already know how to sail?  Rent a 22ft sailboat and create timeless memories as you cruise around Montauk.  Half or full day rentals.