Private Charters

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Private Sailing Charters

Taste of Sailing

Taste of Sailing

Sail with our Captain and experience what it's like to crew on a sloop. Hoist the sails, trim the sheets, take the tiller, or just sit back with a cool beverage in hand. Our sailing trips and tours are hands on, so do as much or as little as you want.

Sail & Swim

Get a Taste of Sailing and some swim time, it's the best of both worlds. Midway through the trip we’ll tie off for a swim and some water games, or relax on the boat with your picnic. Waterguns and pool noodles are kept on board, and we encourage cannonballs, so make a splash!

10am and 2pm

Sail & Swim

Flotilla Boat Parties

Flotilla Boat Part ies

For larger groups, book multiple boats and sail alongside each other flotilla style. Raft up for a picnic and swimming, have a water-fight or win a head to head race.

Flotilla sails are perfect for bachelorette parties, family reunions, corporate events, and team building workshops.

3 hour sail

Sunset Sail

Enjoy a beautiful Montauk sunset on your very own private sail. Like all of our sails, participate as much or as little as you want. Nibble on some snacks, listen to a custom playlist and sip champagne with your sweetheart or loved ones.

Sunset Sail

Get a Taste of Sailing

Bareboat Rentals

Already know how to sail? Rent a Catalina 22 sailboat for some day sailing. Create everlasting memories when you Sail Montauk.

Half day

9am-1pm, 1pm-5pm

Full Day

9am-5pm

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