Private Montauk Sailing Charters

Discover Your Private Escape on the Water with SailTauk

Craving a truly intimate, fully private sailing charter in Montauk? SailTauk delivers personalized, stress-free sails aboard the Barbara Bell across the serene waters of Lake Montauk and the stunning open expanse of Block Island Sound.

Every charter departs right from the prestigious Montauk Yacht Club on Star Island, treating you to constantly shifting, postcard-perfect views: shimmering Lake Montauk, chic Navy Beach, peaceful Fort Pond Bay, historic Gardiners Island, and the distant, iconic Montauk Point Lighthouse standing watch.

Tailor your perfect day:

• Relaxed daytime cruises

• Golden-hour sunset sails

• Sail & swim adventures

• Special celebrations or milestone moments

Bring your own food, drinks, and playlist—enjoy exactly what you love, with complete privacy and comfort. Transparent pricing means no surprises, no hidden fees—just pure, effortless enjoyment.

Every SailTauk charter is fully equipped and ready for you:

• A USCG-licensed captain who knows these local waters intimately

• A spacious, shaded cockpit with ample room to stretch out, lounge, and soak it all in

• A fully stocked cooler with plenty of ice, bottled water, cups, and a bottle opener

• A premium four-speaker Bluetooth sound system to set the mood with your favorite tunes

• Pool noodles and playful water toys for splashing, swimming, and maximum fun on the water

Step aboard for a private sailing experience centered on relaxation, connection, and the simple joy of being on one of the world's most beautiful stretches of coastline.

Welcome to SailTauk—where your Montauk memories become unforgettable. Let's set sail.