Sail Montauk

(4 activities)
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    Private Sunset Sail

    We know you've had a rough week. The 9-5 grind can really get to you after a while. We invite you to seas the day, get on a boat, and relax. Join Sail Montauk for a Sunset Sail experience! You'll learn from the boat's captain and experience what it's like to be crew on a sloop.You'll take part in a hands-on sailing experience doing things such as hoisting the sails, trimming the sheets, and taking the tiller. You can participate as much or as little as you want, and since you'll be sailing at sunset, make sure to bring your significant other to enjoy an evening of romance! Best part? It's a BYOB, and Sail Montauk provides coolers with complimentary ice, so feel free to relax and unwind with cool beverages and snacks! After all, champagne and sailing at sunset is a pairing that would be absolutely sinful not to take advantage of! Soon you'll be able to admit...You're an aqua-holic.
    Private Sunset Sail

    32 Star Island Rd, Montauk

    • Learn from the boat's captain and experience what it's like to be crew on a sloop
    • Hoist the sails, trims the sheets, and take the tiller at sunset
    • Take advantage of the BYOB rules and enjoy some champagne at sunset
    • Get a hands-on sailing experience unlike any other
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    Private Sail & Swim Charter

    We know you've had a rough week. The 9-5 grind can really get to you after a while. We invite you to seas the day, get on a boat, and relax. Join Sail Montauk for the Sail & Swim experience! You'll sail with the boat's captain and experience what it's like to be crew on a sloop.You'll take part in a hands-on sailing experience doing things such as hoisting the sails, trimming the sheets, and taking the tiller. Midway through your personal sailing session, you'll tie off for a swim and take part in some water games! Waterguns and pool noodles are kept on board, so no need to bring your own. Cannonballs are encouraged! And don't worry about a lunch break because you'll have plenty of time to refuel! It's BYOB, and Sail Montauk provides coolers with complimentary ice, so feel free to relax and unwind with a cool beverage and snacks. You can also pack a picnic and have lunch on board! Soon you'll be able to admit...You're an aqua-holic.
    Private Sail & Swim Charter

    32 Star Island Rd, Montauk

    • Learn from the boat's captain and experience what it's like to be crew on a sloop
    • Tie off for a swim and play some water games
    • Pack a picnic and have lunch on board while indulging in some adult beverages
    • Get a hands-on sailing experience unlike any other
    BOOK NOW ← Back
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    Private Sailing Charter

    We know you've had a rough week. The 9-5 grind can really get to you after a while. We invite you to seas the day, get on a boat, and relax. Join Sail Montauk for a Taste of Sailing experience! You'll sail with the boat's captain and experience what it's like to be crew on a sloop.You'll take part in a hands-on sailing experience doing things such as hoisting the sails, trimming the sheets, and taking the tiller. But worry not, you'll have plenty of time to refuel! It's a BYOB, and Sail Montauk provides coolers with complimentary ice, so feel free to relax and unwind with cool beverages and snacks. Soon you'll be able to admit...You're an aqua-holic.
    Private Sailing Charter

    32 Star Island Rd, Montauk

    • Learn from the boat's captain and experience what it's like to be crew on a sloop
    • Hoist the sails, trims the sheets, and take the tiller
    • Sit back with a cool beverage in hand or munch on snacks
    • Get a hands-on sailing experience unlike any other
    BOOK NOW ← Back
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    Learn the Ropes Sailing Workshop

    Finding something fun to do can be a knotty problem. But we've got just the solution! Head on over to this Learn the Ropes Workshop with Sail Montauk! You'll get a dockside, hands-on experience as you learn the basics of sailing. You'll cover basic parts of the boat and their functions, sailing knots, rigging, and hitches. You'll have plenty of time to ask questions to your knowledgeable instructor and experienced sailor -- it's great for both new sailors and salty dogs looking for a refresher. We are knot lying, this is a must-attend for all sailing enthusiasts!
    Learn the Ropes Sailing Workshop

    32 Star Island Rd, Montauk

    • Get a hands-on experience learning the basics of sailing during a dockside workshop
    • Cover basic parts of the boat and their functions, sailing knots, and hitches
    • Ask plenty of questions to become a well-informed amateur sailor
    • Discover or refresh yourself on the art of knot-tying
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