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The top boating charters in Southold

Southold

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Set sail with North Fork Adventures Charters, a 2001 Parker 2510 Pilothouse offering unforgettable boating experiences from Southold! 

North Fork Adventures Charters

Step aboard The Blue Fin IV, a beautifully restored 1968 Custom Ray Chi Chi 41 Sportfish, expertly refurbished in 2019 and based in scenic Greenport. 

Blue Fin IV Lighthouse Cruises and Eco Tours

Embark on a luxurious and unforgettable journey with One More Drift Charters, operating a beautifully restored 1989 Viking Convertible Sportfish, based in scenic Clinton. 

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Come Sail with Captain Joy! 

Looking for an unforgettable experience on the water? 

Joyride Charters

Experience timeless elegance and adventure aboard Montauk Venture Charters, a beautifully restored 1961 Hatteras Sportfish Motor Yacht, fully refreshed in 2020. 

Montauk Venture Charters

Step aboard CrunchTime Sport Fishing, a fully restored 1978 Rose Brothers Custom Charter Headboat, designed for comfort and performance. 

Crunch Time Sport Fishing

  SEA LOVER is a 2019 GALEON 510 Sky Deck Motor Yacht based in Sag Harbor. 

2019 Galeon 510 Sky Deck

Set sail with VitaminSea Voyages, a premium boating experience departing from the scenic shores of Montauk aboard a 2011 Steiger Craft Miami Cuddy Cabin. 

VitaminSea Voyages

Step aboard the legendary CUJO, a beautifully restored 1977 Bertram Sportfish Sportfishing yacht, now better than ever after a full 2025 refit. 

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Discover the perfect getaway on the water aboard Nightjack, a 2002 Levy 32sc Cruiser docked in Stonington. 

Southold: 15 boats available

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Southold: 15 boats available