Montauk Sailing Charters

Set Sail in Montauk

Come aboard one of our two 27′ Stiletto Catamarans in Montauk and enjoy a stable ride that only catamarans can offer. Each sailboat can accommodate 6 guests, making this the perfect venue for smaller groups, couples, and families. Charter both catamarans for day of tandem sailing with up to 12 guests. Add in our popular water trampoline for a truly one-of-a-kind day on the water!

2 Hour Day Sail – $250.00 + gratuity for the first 2 passengers; $60.00 for each additional person
3 Hour Day Sail – $350.00 + gratuity for the first 2 passengers; $75.00 for each additional person

All sailing charters are operated by a professional USCG-licensed captain. Connect to our premium bluetooth stereo to jam out to your favorite tunes and enjoy an ice cold drink with great company. Feel free to bring your own food and beverages, and we’ll bring the good vibes! 

Call (631) 668-8079 for half-day charters & custom pricing

Featured Sailing Charters in Montauk

Catamaran Day Sail in Montauk

Experience one of our two 27’ Stiletto Catamarans. A fast yet stable ride, both of our Catamarans offer an exciting sail with no heeling. Passengers can relax on deck while taking in the sights, lend a hand at the helm, or lay back on the front canopy while the water rushes beneath you. Limited to 6 passengers, you’ll enjoy an intimate and highly customizable sailing experience. Half and Full Day Sailing Charters are also available – give us a call for more information.

Catamaran Sail + Swim

Relax in the sun and lay out as the water rushes beneath you. Choose the 3 Hour Day Sail to give yourself plenty of time to sail and stop at a beach to cool off in the waters of Montauk, or anchor up to our 20′ water trampoline and slide for a truly unique experience. Each vessel can carry up to six passengers and all tours are guided by a professional USCG-licensed captain. 

Sunset Sail Montauk

Montauk Sunset Sail

Our most popular sailing charter, watching a sunset during a leisurely sail in Montauk is the perfect way to end your day, or begin your evening. Bring a bottle of your favorite beverage to toast the sun’s departure or ring in the evening’s festivities.

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