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The top boating charters in Southold

Southold

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

2019 Galeon 510 Sky Deck

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

Montauk Charterboat CUJO

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

Nightjack

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

One More Drift 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

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

Crunch Time Sport Fishing

D.C. OUTDOOR ADVENTURES is a 2022 Parker 2820 Pilothouse based out of Mastic. 

D.C. OUTDOOR ADVENTURES

Come Sail with Captain Joy! 

Looking for an unforgettable experience on the water? 

Joyride Charters

Step aboard Steal Your Fish Charters, LLC, a sleek and powerful 2015 Boston Whaler Outrage Center Console based out of New London. 

Steal Your Fish Charters, LLC

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

Southold: 15 boats available

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Southold: 15 boats available